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THE 10 BEST Chicago Tours & Excursions

Chicago tours.

• Sightseeing Tours
• Historical & Heritage Tours
• Cultural Tours
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• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Chicago Architecture River Cruise

2. Chicago River 90-Minute Architecture Tour

3. Chicago River 45-Minute Architecture Tour from Magnificent Mile

4. Chicago: Gangsters and Ghosts Walking Tour

5. Chicago Architecture Center River Cruise aboard Chicago's First Lady

6. Chicago Crime and Mob Bus Tour

7. Chicago Favorites Food & Walking Tour plus FREE Bike/Kayak Rental

8. Skydeck Chicago Admission Ticket

9. Chicago Guided Cocktail Cruise

10. Flyover in Chicago

11. Chicago River Boat Architecture Tour

12. Chicago in a Day: Food, History and Architecture Walking Tour

13. 360 CHICAGO Observation Deck Admission

14. Big Bus Chicago Hop-On Hop-Off Sightseeing Tour

15. Chicago Lake Michigan Sunset Cruise

16. 2-Hour Guided Segway Tour of Chicago

17. Chicago CityPASS®

18. Chicago Gangster and Food Walking Tour

19. Chicago Walking Food Tour With Secret Food Tours

20. Chicago City Minibus Tour

21. Chicago Buffet Lunch Cruise on Lake Michigan

22. Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

23. Insta Walk and Polaroid Photoshoot in Chicago

24. Field Museum of Natural History Admission Tickets

25. Chicago Craft Brewery Barrel Bus Tour

26. Chicago Lake and River Architecture Tour

27. Lake Michigan Skyline Cruise in Chicago

28. Chicago Pizza Tour

29. Chicago's Chinatown Food and Walking Tour

30. Blue Man Group at the Briar Street Theater in Chicago

What travelers are saying.

• Chicago Architecture River Cruise
• Chicago River 45-Minute Architecture Tour from Magnificent Mile
• Chicago River 90-Minute Architecture Tour
• Gangsters and Ghosts Tour in Chicago
• Chicago Crime and Mob Bus Tour
• Inside Chicago Walking Tours
• Chicago Greeter
• Bobby's Bike Hike Chicago
• Tours With Mike
• Babylon Tours Chicago
• Pizza City USA
• Chicago Private Tours
• Free Chicago Walking Tours
• Chicago's Finest Tours
• Walk Chicago Tours
• Absolutely Chicago Segway Tours
• Chicago Elevated
• 3rd Coast Charters
• Steve's Segway Tours
• Urban Kayaks
• City Cruises Chicago
• Windy City Sailing

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The 14 Best Chicago Tours

Foodies, architecture buffs and historians alike will appreciate these tours of the Windy City.

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There are a variety of ways to see Chicago's best sights.

Note: Some tour providers on this list may have limited or ceased operations due to COVID-19. Check with your tour operator about availability before you book.

One of the best ways to sightsee your way through a new city is with the help of a local. With this in mind, U.S. News rounded up 14 of Chicago 's best guided tours. Whether you're sailing past Willis Tower on a river cruise or sampling some of Chicago's best deep-dish pizza on a foodie excursion, you'll gain a cultural and historical understanding of the Windy City during these tours.

Chicago Food Planet – Gateway to the West Loop Food Tour

Chicago Food Planet's Gateway to the West Loop spotlights some of the tastiest dishes in the city – specifically pizza, doughnuts and burgers. The three-hour tour centers on the West Loop neighborhood's incredible food scene and provides insider insights to the history and culture of the area. Guides regularly win praise from travelers for their knowledge and enthusiasm. Ticket prices start at $65 for adults and $50 for children ages 12 and younger. Reviewers find the tour worth the price for the generous amounts of food provided. What's more, group sizes are restricted to 14 people and tours do not involve extensive walking. Tours are offered Thursday through Sunday at 1 p.m. Chicago Food Planet also offers tours of Chicago's Chinatown neighborhood.

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Absolutely Chicago Segway Tours – Chicago Lakefront/Museum Campus

The Chicago Lakefront/Museum Campus tour offered by Absolutely Chicago Segway Tours showcases many of the city's most popular attractions , including Millennium Park (the starting point), Grant Park, Monroe Harbor, the Field Museum, Shedd Aquarium , Soldier Field and the Adler Planetarium. The 8-mile journey on easy-to-ride, two-wheeled, battery-powered vehicles lasts approximately 2 1/2 hours. Participants praise tour guides for their insight and professionalism. Tickets cost approximately $65, depending on date and time. Note that riders must be at least 12 years old. Tours are available daily. The company offers several other tours, some centered around other parts of the city or with specific themes like architecture, crime and ghosts.

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Inside Chicago Walking Tours – Dazzling Interiors of the Loop

Inside Chicago Walking Tours' The World Within: Dazzling Interiors of the Loop tour reveals interior architectural details that visitors might otherwise miss. Highlights of the two-hour tour include a gilded 80-foot-high ceiling, art deco lobbies, early Frank Lloyd Wright designs and rooms with stained-glass mosaics. Reviewers describe this tour, which involves about 1 1/2 miles of walking, as an informative and entertaining way to learn about the history of Chicago and its diverse, distinctive buildings. Tickets start at $30 for participants 11 and older and $25 for children ages 5 to 10 and patrons 65 and older. Children ages 4 and younger tour for free. Outings run Saturdays at 11 a.m. Inside Chicago also offers other architecture-oriented tours as well as private tours.

Courtesy of Bobby's Bike Hike Chicago

Bobby's Bike Hike offers several different tours, including a 13-mile Bikes, Bites & Brews tour.

Bobby's Bike Hike Chicago – Bikes, Bites & Brews Tour – Signature Dishes

This triple threat tour combines bicycling, food and beer. The four-hour, 13-mile ride traverses the Gold Coast, Lakeview, Wrigleyville and Lincoln Park neighborhoods with stops for pizza, beer, cupcakes and hot dogs. Reviewers find the tour provides a great introduction to the city and rate the guides highly. Tickets for adults, which include the bike rental as well as food and drinks, start at $76.99 for weekday rides (weekend rides are slightly more expensive). Participants must be at least 21 years old. If you're traveling with kids, try Bobby's Bike Hike Chicago's Family Food & Bike Tour.

Chicago Pizza Tours – Original Chicago Pizza Tour

Experience one of Chicago's unique culinary phenomena with the Original Chicago Pizza Tour. On this 3 1/2-hour tour, you'll visit four independently run neighborhood pizzerias and sample six or more slices. Many reviewers praise the informative and entertaining tour guides. Others insist that the tour is about more than just pizza and encompasses Chicago history, architecture and culture. Tickets start at $60 for adults and $36 for children. If you're interested in exploring the city's pizza from other angles, you can take one of the company's other food tours, which combine pizza and cocktails or focus on the city's biggest slices.

Courtesy of Big Bus Chicago

Big Bus Chicago's tours give tourists the opportunity to see Chicago's sites at their leisure.

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago's Hop-On Hop-Off Tours permit guests to tailor excursions to their preferences by allowing them to spend as much time as they want at any of the 12 stops within the eight hours of the standard package. Tour-takers can "hop off" a bus and spend time at popular destinations like Skydeck Chicago , Navy Pier, Soldier Field or Millennium Park and then "hop on" a later bus. Buses run every 30 to 45 minutes and include guides that provide commentary. Travelers frequently describe guides as entertaining and informative. One pain point for riders is the signage: some found it difficult to locate the bus stops at certain attractions. Ticket prices start at $49 for adults and $30 for children (though you may be able to score a discount by purchasing online in advance). In addition to its classic ticket, Big Bus Chicago offers a premium ticket valid for two days.

Tastebud Tours – Taste of Chicago

Tastebud Tours' Taste of Chicago explores the city's downtown Loop area. The three-hour tour includes stops at multiple restaurants and shops for distinctive Chicago deep-dish pizza, popcorn, sandwiches and sweets. The tour also highlights non-food-related landmarks like the Chicago Cultural Center, the Art Institute of Chicago and the Marshall Field and Company Building, which visitors tend to appreciate. Guides consistently win praise for their knowledge of and enthusiasm for Chicago history. Tickets, which start at $59.50, include all food. (Adult beverages can be purchased separately where available.) Groups are limited to 18 people. Tastebud Tours also offers other food-centric excursions as well as private tours.

Chicago Architecture Foundation River Cruise

The Chicago Architecture Foundation's River Cruise ferries guests along the Chicago River as docents from the Chicago Architecture Center regale them with the stories behind more than 50 notable buildings. The volunteer docents repeatedly win high praise from reviewers for their in-depth knowledge of the city's history and its structures. The cruising vessels, part of the Chicago's First Lady Cruises fleet, can carry up to 250 people and boast full-service bars and open-air upper decks. Tickets for the 90-minute excursions cost around $45 for daytime cruises. Twilight outings are a few dollars more. For an additional $5, you can also gain admittance to the Chicago Architecture Center (which usually costs $12 on its own).

Courtesy of Chicago Prohibition Tours

Guides on Chicago Prohibition Tours can offer travelers suggestions on Prohibition-inspired drinks to order

Chicago Prohibition Tour – Original

Chicago Prohibition Tours explore a notoriously eventful moment in the city's history. Its flagship offering visits the sites of four former speakeasies via bus over the course of 3 1/2 hours. Guides provide historical information and share what kinds of drinks would be representative of those consumed illicitly during the Prohibition era. Additionally, you will be driven from location to location by the company. Reviewers rave about the fast-talking guide and say this is an experience both locals and visitors will enjoy. Others appreciate that each bar on the tour is unique. Tickets, which start at $55, do not include food or drinks, which can be ordered separately at tour-takers' discretion. There is also a walking version of this tour that lasts 2 1/2 hours.

Urban Kayak Chicago Riverwalk – Historic Chicago Tour

For a "duck's-eye," up-close view of the city, take Urban Kayak's Historic Chicago Tour. Starting at the Riverwalk , tour-takers paddle their kayaks on the main branch of the Chicago River with periodic stops at points of historical interest, where guides provide information regarding the city's famed architecture. Reviewers say this is a great experience, even for beginners. Meanwhile, others note that the experienced guides are skillful at navigating boat traffic. Tickets cost approximately $65 for a single kayak or $130 for a tandem (two-person) kayak for the approximately two-hour tour. Urban Kayak also offers kayak rentals and paddleboarding classes.

Shoreline Sightseeing – Skyline Lake Tours

Shoreline Sightseeing Skyline Lake Tours offer unrivaled views of Chicago's skyline, and many photo opportunities, via cruises along the Lake Michigan shoreline. The 6-mile trip provides views of notable landmarks, such as the John Hancock Center, the Willis Tower (aka the Sears Tower), Adler Planetarium and the Field Museum . According to reviewers, these iconic buildings are much more visible from the water than they are on the street. Many say this tour was the highlight of their Chicago trip. Tickets for the 40-minute, narrated boat rides start at $23 for adults and $8 for children ages 3 to 12. Kids 2 and younger ride free. Travelers can purchase drinks at the onboard cash bar. Shoreline Sightseeing also offers architecture-focused tours along the Chicago River.

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Ken Flisek | Courtesy of Tall Ship Windy

The Tall Ship Windy provides tourists an enjoyable sailing and sightseeing experience.

Tall Ship Windy – Chicago Skyline Sail

Tall Ship Windy's Chicago Skyline Sail features views of the city from the deck of a 148-foot, four-masted schooner. Reviewers tout the remarkable views of the city's impressive structures and, weather-permitting, the special experience of being able to actually sail and not rely on the boat's motor. What's more, tour participants commend the crew members for their professionalism. Tickets for the summer and fall excursions start at $37 for adults and $17 for children ages 12 and younger; infants 12 months and younger ride for $1. Tall Ship Windy has a full bar on board (drinks are not included in the ticket price.) In addition to the daily 75-minute excursions, Tall Ship Windy offers fireworks cruises on select dates as well as pirate-themed outings.

Chicago Crime Tours

Chicago Crime Tours explore famous crime scenes in a variety of Chicago neighborhoods, including the Gold Coast, Lincoln Park, the Loop, the Magnificent Mile , Old Town and River North. The bus tour, which lasts about two hours, includes stops at the spots where gangsters like Hymie Weiss were killed as well as the site of the St. Valentine's Day Massacre. It also visits locales associated with Al Capone, Frank "the Enforcer" Nitti and Leopold and Loeb, among others. Reviewers laud the tours for providing a unique angle on Chicago's colorful history. Tickets cost approximately $40 and can be purchased in advance (advised) or on the bus. A nighttime crime tour and a pizza and crime walking tour are also available.

City Cruises by Hornblower – Seadog Lakefront Speedboat Tour

Zip across Lake Michigan during this high-speed, musically enhanced 30-minute tour. During the ride, you'll see striking views of the Chicago skyline and hear some descriptions of the sights. Visitors praise the crew's knowledge and charisma. They also enjoy whipping along the waves. Tickets cost about $30 for adults and $20 for kids ages 3 to 12. Children ages 2 and younger ride free, but do require a ticket. The boat is open-air, which means travelers might get wet. City Cruises runs a myriad of other boating adventures, including an extreme thrill ride.

You may also be interested in:

• The Best Chicago Walking Tours
• The Best Chicago Segway Tours
• The Best Chicago Boat Tours
• The Best Things to Do in Chicago
• The Best Hotels in Chicago
• The Top Romantic Getaways in Illinois

Tags: Chicago , Travel , food and drink , Vacations , Tours , Illinois Vacations , Midwest Vacations , US Vacations

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Home » Travel Guides » United States » Illinois (IL) » 15 Best Tours in Chicago (by a Local)

15 Best Tours in Chicago (by a Local)

The Windy City is the third largest city in the United States and comes with a variety of delights for any visitor. From food and craft beer to architecture and history, the Midwestern metropolis is packed with exciting experiences.

There are a variety of great tours run by locals across the city that help you dive deep into the things that matter most to Chicagoans. The unique history and culture of the city is best discovered with a local guide, and these tours will help you to dive deeper into what makes the city tick.

I’m a Chicago local and have been on many tours with friends and family visiting. To get you started here’s my list of the best tours in Chicago.

1. Chicago Skydeck + “The Ledge” Experience Ticket

The Willis Tower is the tallest Skyscraper in Chicago and this ticket allows you to go to the very top.

There are a bunch of exhibits on the way, to teach you about Chicago’s history and the deep cultural roots that connect the city. Once at the top, brave visitors can step into ‘the Ledge,’ a series of four glass balconies that give you views across Chicago as well as over the street below.

A theatrical presentation is also included in the ticket, which discusses the construction of the Willis Tower.

2. Chicago River Architecture Cruise

For a more relaxing tour experience, this river cruise takes you down the Chicago River whilst also discovering the architecture of the city and the history behind some of the most iconic buildings.

The 75-minute-long tour passes more than 40 different monuments, as well as a variety of the city’s most well-known bridges.

The commentary is provided by a live guide on board the ship, and there is a bar available for you to purchase refreshments and drinks. This is actually one of the tours I personally like most for first-time visitors. You can also check out my guide on the best boat tours in Chicago .

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3. Wicker Park Walking Food Tour

Like many cities across the United States, Chicago is well known for its growing food culture and Wicker Park is a hub for the culinary scene in the city. This three-hour tour is conducted by a local with extensive knowledge of the best food to try in the city.

You will sample typical Chicagoan food from five different restaurants in the area, all offering their own little slice of the city. This is a great dinnertime tour that will provide you with more than enough food to make a full meal, so come with a full appetite.

4. 90-Minute Mob and Crime Bus Tour

Discover the dark underbelly of Chicago from the safety of a tour bus with this tour, which tackles the history of mobsters and criminals in the city.

You will learn about Al Capone, John Dillinger and many other famous criminals from the city in this tour which lasts around 90 minutes.

You will be shown the different sites that have been influenced by crime in the city, and be able to follow in the footsteps of the most notorious mobsters. You can also delve deeper into the history of the subject at the small mobster museum located in the city.

5. Treasures of Chicago’s Golden Age: 90-Minute Walking Tour

The city experienced a major boom in the late 19th century, which extended right through to the early years of the following century.

This tour takes you around all of the architectural highlights from the era when the city was in major expansion and people were flocking from across the United States to the Windy City. Your skilled local guide will discuss the different factors that influenced Chicago’s expansion, as well as highlight the important historical events that still shape the city to this day.

This tour focuses on the people that built Chicago, giving it a nice personal touch. I highly recommend taking a walking tour on the first day of your visit, it offers plenty of tips on what to do the coming days as well.

6. Chicago Secret Food Tour

Chicago is full of famous restaurants and bars, however this tour aims to take you to the best restaurants that are not well-known by visitors.

You will visit six different spots around the Loop District of Chicago, and learn about the important influence Italian immigrants had on the city. The walking tour takes around three hours to complete, and is paced so you can truly savor all of the dishes you are sampling.

Some drinks are also included. The tour also discusses the local art and architecture in the area, making it a great tour for your first evening in the city.

7. Loop Interior Architecture: 2-Hour Walking Tour

This tour takes you inside the most famous buildings to talk about how the magnificent architecture has been taken indoors.

You will get an extensive tour of the entrances and corridors of these buildings from a knowledgeable local guide, who will discuss the history found within their walls and the lives of the architects who designed them.

You will also be able to check out the underground Pedway System, which has shaped how the rest of the city was designed and changed the lives of locals for decades.

Related reading :  Best Things to Do in Downtown Chicago

8. Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe

Hop-on-hop-off bus tours are a great way to become acquainted with a new city and gather your bearings. This tour takes you to all of the main sights in the city for you to explore at your own pace.

Audio guides are included to give you more information, and these are available in multiple languages. You can customise your ticket to last either one or two days, and to also include a night bus option. Free WiFi is available on all of the buses, and all guests are given a free bag of Garrett’s Popcorn to snack on whilst enjoying the tour.

I recommend it as a great way to get around the city during your entire visit (there’s 24, 48 and 72 hour option).

9. Gourmet Brunch, Lunch, or Dinner River Cruise

Delight your taste buds with a scrumptious meal prepared by talented chefs, offering a variety of brunch, lunch, or dinner options. Knowledgeable guides provide captivating commentary on the city’s history and architectural wonders, showcasing landmarks like Willis Tower and Navy Pier.

This unique blend of exquisite cuisine, breathtaking scenery, and informative narration promises an unforgettable journey through Chicago’s heart.

Read next :  15 Best Day Trips from Chicago

10. Chicago’s Modern Skyscrapers Guided Walking Tour

Chicago has some of the highest skyscrapers in the city. If one of your main aims for your trip is to check them out, then this walking tour can help you take in the most famous buildings in Chicago.

The local guide will help you understand the history behind all of the skyscrapers, as well as talk at length about the innovations made by architects in the city.

You will learn more about the modernist movement that shaped the city’s skyline and still influences new buildings to this day.

11. Private Helicopter Flight

For the ultimate nighttime tour of the city, this helicopter experience is a fantastic option if you are looking to splurge.

The pilot is fully licensed and experienced, and comes from the local area so is able to provide high-quality commentary about all of the sights you can see from the sky.

From skyscrapers, to the wild waves of Lake Michigan, you can truly see it all from this helicopter experience. All safety equipment is provided and customers are given a short briefing before take-off. Might be an obvious tip but I recommend this experience during a clear day.

12. Navy Pier Centennial Wheel

The Chicago Navy Pier Centennial Wheel offers an exciting experience at one of the city’s most iconic landmarks. With this tour, visitors can enjoy stunning views of Chicago’s skyline and Lake Michigan from the impressive Centennial Wheel. The tour provides various ticket options, allowing guests to customize their experience.

Whether opting for a standard ride, a fast pass, or a private gondola, I highly recommend it to take in breathtaking panoramic view of the city.

Related :  15 Best Hotels in Chicago

13. Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour

Featuring some of the wealthiest districts in Chicago, the Lakefront Neighborhoods Tour can provide a relaxed and fulfilling experience during your stay in Chicago.

This tour is done on bikes, helping you to enjoy a more active adventure as well as explore the neighbourhoods at an easy pace. You will be able to check out the local mansions, as well as the Lincoln Park Zoo.

The Lakeside area, where the tour ends, is also a good spot for photo opportunities. This tour accepts all ages, making it a good option for families.

14. Chicago South Side Tour with Optional River Cruise

For visitors more interested in the history of the city, the South Side region is definitely worth a visit.

In this tour, a local guide will talk to you about the founding of the city, and the important landmarks in the South Side region that display the complex and vibrant history of Chicago.

You will also be taken to Jackson Park to enjoy some recreational activities, and to the Art Institute to see the world’s largest collection of Impressionist Art.

This two-hour tour finishes up at the University of Chicago, where you can enjoy the ornate English architecture.

15. Chicago Haunted Bar Tour

Most major American cities have their ghost stories, and Chicago is no exception. Learn all about the macabre past of Chicago and hear captivating ghost stories along the way.

This tour takes you to four different bars across the city, where you can spend some time soaking up the atmosphere and enjoying a local beverage. The tour lasts around two and a half hours, and is great if you are looking for a unique night out in the city.

15 Best Tours in Chicago (by a Local):

• Chicago Skydeck + “The Ledge” Experience Ticket
• Chicago River Architecture Cruise
• Wicker Park Walking Food Tour
• 90-Minute Mob and Crime Bus Tour
• Treasures of Chicago’s Golden Age: 90-Minute Walking Tour
• Chicago Secret Food Tour
• Loop Interior Architecture: 2-Hour Walking Tour
• Chicago Hop-on-Hop-off Bus Tour: Classic, Premium or Deluxe
• Gourmet Brunch, Lunch, or Dinner River Cruise
• Chicago’s Modern Skyscrapers Guided Walking Tour
• Private Helicopter Flight
• Navy Pier Centennial Wheel
• Bobby’s Bike Hike Chicago: Lakefront Neighborhoods Tour
• Chicago South Side Tour with Optional River Cruise
• Chicago Haunted Bar Tour

Chicago Tours

Chicago is a sprawling city, comprised of dozens of neighborhoods with unique characteristics and singular attractions. It can be hard to approach exploring the city without an insider’s knowledge of the best way to get to Wicker Park, or the top pizza place in River North. Fortunately, there’s a wide variety of tours available in Chicago to help visitors make the most of their time in the city while easily navigating the best attractions, areas, and cuisines.

For first-time visitors, bus tours are a smart option. They can help you see more of the city than you would be able to via mass transit (without some very complex planning, that is). Bus tours also allow you to see the highlights of the city via a pre-planned route that maximizes sightseeing potential and minimizes driving time. Hop-on hop-off options are key here, too, as they facilitate exploring the city at your own pace, and visiting attractions that pique your interest from the bus. There are even themed bus tours that cover topics like food, drink, and Chicago culture.

Chicago boasts many types of tours beyond the typical bus tour, however. If you’d like to experience Lake Michigan or the Chicago River – two essential components to the city’s identity – then a boat tour is a smart option. You can choose a tour that simply showcases the lake, or one that highlights city architecture. Visitors can also opt to explore the via bike: take a guided tour or explore on your own. Given that Chicago is a very walkable city, it’s unsurprising that another popular type of tour is a walking tour. These are usually themed around a concept like food, drink, pop culture, local legends, and more. The Chicago Architecture Center also runs many architecture-specific tours, and many companies offer guided tours (on foot or via bus) related to culinary concepts.

Whatever kind of tour you’re interested in, you’ll find a number of excellent options in Chicago. Here’s an overview of the most popular tour types in Chicago.

The classic option for exploring Chicago, bus tours come in a variety of styles ranging from guided tours of the North and South Sides to fully-narrated hop-on hop-off tours.

With Lake Michigan and the Chicago River being so important to the city, it’s no surprise that you can tour the city via boat. Choose a theme, or just enjoy the sail.

Explore the city in an eco-friendly way by making your way through the parks and trails of Chicago on two wheels. Take a self-guided tour, or opt for the full experience.

Walking Tours

In spite of its massive size, Chicago is the ideal city for a walking tour. Explore a neighborhood, a theme, a concept, or a story on these guided excursions.

If you’re interested in Chicago’s culinary scene, then a food tour is a must. They’re organized around neighborhoods or cuisines and are perfect for foodies.

Architecture Tours

Chicago’s architectural legacy is among the best in the country. Enjoy the amazing, inspiring buildings that populate the city skyline on an architecture tour.

Tour Companies

Gray line chicago.

Gray Line Tours offers 5 different tour options in Chicago. Popular Gray Line Chicago tours include the Chicago Grand City tour, the Chicago North Side tour, and the Historic Chicago South Shore tour.

Chicago Crime Tours

Takes visitors on guided outings to a number of famous crime scenes. Along the way, guests will learn about Chicago’s history as a hotbed for criminals like John Dillinger, Al Capone, and more.

Bike and Roll Chicago

Offers a variety of guided bike and Segway tours that take visitors to a number of Chicago’s most iconic attractions. They also offer bike rentals by the hour or day.

Tall Ship Windy

Based out of Navy Pier, Tall Ship Windy operates a variety of scenic cruises on its approximately 150-foot schooner. Popular tours include the Lakeside Architecture Sail and the Skyline Sail, with several other options available.

Big Bus Chicago

With their distinctive fleet of open-top, double-decker buses, Big Bus Chicago offers hop-on, hop-off tours that let you choose where and when you stop at a given attraction.

Shoreline Sightseeing

Has been running scenic tours of Chicago along Lake Michigan and the Chicago River for 80 years. Their most popular tours include a river excursion highlighting Chicago’s acclaimed architecture and a lake cruise departing from Navy Pier .

25 Things to Do in Chicago (from a Local!)

09/20/2022 by Emily Becker Leave a Comment

This post was written by Emily Becker, a Chicago native freelance writer for BMTM.

If you’re looking for things to do in Chicago, the list can get pretty long and overwhelming. After all, it’s a huge metropolis with 2.7 million people living in it. To make your Chicago trip planning a little easier, I’ve narrowed it down to the 25 absolutely essential things that you can’t leave the city without doing. From the quintessential Bean selfie to the best places to grab a bite or catch a show, these are my top picks, as a Chicago native:

Table of Contents

Year-Round Things to Do in Chicago

When you’re deciding when to visit, don’t get trapped by all the hype around the Chicago summer. There are plenty of things to do regardless of the season, and these are some of my favorites:

1. Take a selfie in the Bean

Although you won’t see native Chicagoans doing this, taking a selfie in the Bean is a rite of passage as a tourist, no matter how silly it seems. The Bean aka Cloud Gate is a massive silver art installation in the middle of Millennium Park in the heart of downtown. For many visitors, this is one of their first stops, as it’s one of the most iconic things to do in town. Since the entire structure is sleek metal, you can snap a selfie in its reflection, which makes for a fun memento of your Chi-town adventure.

Visiting Millennium Park is one of the many free things to do in Chicago , and you can explore the surrounding area, which is bustling any time of year but especially in the summer, when there are festivals there on the weekends.

2. Try deep-dish pizza

Another semi-cliché addition to your list of things to do in Chicago is getting your hands on a slice (or a whole pie!) of deep-dish pizza. I don’t mean just any deep-dish pizza, though. If you ask a native Chicagoan where they get their fix, chances are it won’t be the big chain restaurants like Giordano’s. My favorite is Pequod’s , because of the crispy caramelized crust on the pies.

3. Go on a food tour

If one slice of deep-dish has your head spinning and you’re dying to try more Chicago delicacies, consider a walking food tour. This will take you on a tasty adventure to try not only deep-dish pizza but other staples, like Chicago hot dogs, Italian beef, and other foods that originated from among various immigrant groups. There are so many different dishes to try, from Polish paczki s to Puerto Rican jibaritos and many more. A food tour is a great introduction to the gastronomical splendor of Chicago, as your guide can provide historical and cultural context to the food in a way that trying them all on your own doesn’t.

4. Explore Mexican culture through food and art in Pilsen

Pilsen is one of Chicago’s multiple neighborhoods that has a large population of Mexican Americans. Here you’ll find colorful street murals with Mexican and Latin American motifs, as well as an abundance of taquerías that are bursting with authentic Mexican flavor. It is also home to one of my favorite places in the city, the National Museum of Mexican Art . This free museum features artwork by Mexican artists young and old, with special exhibits on rotation throughout the year.

To get to the heart of Pilsen, take the Pink Line train to the Pilsen stop. From there you can easily explore the neighborhood on foot. In the last decade or so, it has undergone a great deal of gentrification, so the district is constantly changing. Try to visit restaurants and cafés run by local families if you can.

5. Catch a film at the Music Box Theatre

In the Lincoln Park neighborhood, you’ll find all kinds of gems, the Music Box Theatre being one of them. This theatre was first built in 1929 and continues to show movies today. With its quirky independent films as well as cult classics and international movies, the Music Box always keeps things interesting. The theatre is especially famous for its yearly rendition of The Rocky Horror Picture Show , so if you visit in the fall, it’s a must-do.

6. Peruse the Art Institute of Chicago

The Art Institute of Chicago is by far one of my favorite places in the whole city. When I was in college, I always went on Thursdays, when there was free admission for students. Being able to walk through the exhibits alone, pausing at anything that caught my eye, was always a treat. I especially love taking a coffee break at the café inside the museum before resuming my leisurely stroll.

The rotating exhibits change every couple of months, giving you something to look forward to throughout the year. Admission is $25 for non-Chicago residents; although the ticket price may seem pricey, you could easily spend an entire morning or afternoon here because there’s so much to see.

7. Laugh all night at The Second City

Chicago’s nickname is “the second city” in reference to its having once been the second-largest city in the US. Although the reference is a bit outdated, the world-famous improv company The Second City makes a joke of the term.

The company is where actors and comedians like Tina Fey and Amy Poehler got their first big break. Nowadays you can see some of the country’s best comedians perform there, with shows almost every night of the week. Tickets range between $40 and $100, with cheaper options on weekdays.

8. Go to Tina Fey’s favorite restaurant: The Athenian Room

If you find yourself in Lincoln Park on Chicago’s Northside (which you should!), don’t pass up the opportunity to have a meal at The Athenian Room . This Greek restaurant is not only a local favorite, but Tina Fey herself boasts that it’s her all-time favorite in Chicago . You won’t find any photos of Tina on the wall, but urban legend has it that she ate there on more than a weekly basis during her Second City days.

Regardless of whether or not you care that this is a celebrity favorite, The Athenian Room is a delightful place to grab a bite. It offers authentic Greek cuisine that is flavorful and affordable, with specialties like whole roasted chicken and whole slabs of feta cheese doused in olive oil and spices.

9. Admire the Tiffany glass dome at the Chicago Cultural Center

The Chicago Cultural Center is another stellar place to visit in the heart of downtown, close to the Art Institute and Millennium Park. Besides being one of the bougiest wedding venues in the city, the Cultural Center is also home to a theatre that screens movies throughout the fall, an exhibition space with art installations, and various events throughout the year.

It’s free to visit, meaning you can walk in just to admire the famous Tiffany glass dome in the ceiling close to the entrance. There are free tours if you want to learn more about the building’s history and architecture as well.

10. Get lost in a maze of stacks at Myopic Books

If you want to experience Chicago from a more local perspective, consider spending time in Wicker Park. This West Side neighborhood is easily accessible via the Blue Line train that you can hop on in downtown. Get off at Damen and feast your eyes on this cool and quirky neighborhood full of fun shops, chill cafés (my favorite is the Wormhole ), and colorful murals.

Myopic Books is a used bookstore with a maze-like feel. It’s a fun place to spend an hour or two getting lost in the stacks and exploring from the basement to the hidden reading room at the very top.

11. Stroll through the Garfield Park Conservatory

The Garfield Park Conservatory is another incredible free place to visit in Chicago , but it’s also one I’d pay to enter if they ever change their mind. It’s the largest conservatory in the city, and one of the most impressive in the whole country due to its outstanding variety of plant species.

Beyond taking a walk through to check out the plants, the conservatory also hosts various events throughout the week. From dance classes to painting workshops and live beekeeping demos, there’s always something interesting going on at the Garfield Park Conservatory during any season. Since the Garfield Park neighborhood as a whole usually falls by the wayside for tourists, visiting the conservatory is a great way to get off the beaten path and serves as a launching point for a neighborhood you might not have otherwise thought to visit.

12. Time-travel at the Green Mill

Since real time travel doesn’t exist yet, the next best thing is visiting the Green Mill in Chicago’s Uptown neighborhood. This old speakeasy turned modern-day jazz cocktail lounge is the ultimate place to get a feel for 1920s Chicago nightlife. Besides ordering a cocktail and listening to live music (any night of the week), the quirks of the Green Mill are enough of a reason to visit.

First of all, this place is cash only, which is an anomaly in such a large city like Chicago. Second, the Green Mill is famous for its witty and sometimes sassy bartenders (don’t even try to order a mojito here — you’ll see why). Although many people scout out the Green Mill to see one of the places where Al Capone allegedly hung out, it’s worth a visit even without the urban legend surrounding it.

13. Listen to blues at Kingston Mines

If you can’t get enough of Chicago’s live music scene, head to Kingston Mines for the ultimate place to listen to blues in Chicago. It’s the oldest continuously running blues club in the city (and hasn’t changed much since it opened in 1968) and has a reputation for bringing some of the biggest names in the genre.

Kingston Mines is open from Thursday to Saturday and has live music throughout the weekend. It’s in Lincoln Park, just a couple of blocks away from DePaul University (my alma mater).

14. See Chi-Town from above

One of the most epic ways to see Chicago from above is to climb to the top of the John Hancock Building to the 360-degree observation deck. Here you can step onto a glass platform suspended 95 floors in the air, with Chicago’s bustling downtown beneath you. This is one of the best adrenaline-pumping activities in the city, with the absolute best views of downtown that you can find. Get your ticket to 360 Chicago here.

15. Grab dim sum in Chinatown

Chinatown is the gateway to Chicago’s South Side. One of the most legendary restaurants is MingHin , which serves traditional Chinese dim sum all day.

Although Chicago’s pales in comparison to NYC’s massive counterpart, it is still worth visiting for a variety of reasons beyond simply grabbing dim sum. Spend some time walking through the district, where you’ll find all kinds of shops with Chinese goods, including specialized tea and herbal shops that are fun to explore. This is also the best neighborhood in which to get your boba fix.

Things to Do in Chicago in the Warmer Months

Visiting anytime from late spring to early fall means a lot more options for things to do in Chicago. From enjoying the Chicago River to catching a Cubs game, these are the best warm-weather activities:

16. Kayak along the Chicago River

If you thought the views of downtown from the bridges over the Chicago River or from the Riverwalk were great, imagine how epic they are from a kayak on the water! I did this activity years ago and absolutely loved it. The freedom to explore on your own is ideal for adventurous travelers, with the added bonus of getting a solid workout in while you do it.

Kayak Chicago has kayaks for rent for $30/hour or $90 for the whole day. You can also book a tour if you’d like a more in-depth experience with a guide.

17. Attend a Street Festival

Summertime is street festival season in Chicago , and there are hundreds to choose from. From the Pride festival every June to Lollapalooza and smaller cultural neighborhood celebrations, visiting Chicago in the summertime guarantees you’ll find something interesting going on in the streets.

I recommend aiming to visit at least one neighborhood festival, as these are more unique and will give you the opportunity to see more than just downtown, where many tourists get stuck. As a local, I think there’s so much more to the city than the skyscrapers and bustle of downtown, so a smaller festival is a great introduction to a neighborhood you might not have on your bucket list.

18. Marvel at Chicago’s architecture on a boat tour

If there’s anything you absolutely have to do during a summertime trip to Chicago, especially if it’s your first time, it’s an architecture boat tour. These give you a full rundown on some of the city’s most impressive buildings, offering valuable historical context for the most notable downtown edifices.

Architecture boat tours are $40-60 per person and typically last around 1.5 hours. Book your Chicago architecture boat tour here .

19. Have a drink on a rooftop…

A summertime must-do is grabbing a drink on a rooftop, with the sparkling city lights all around you. One of the most popular rooftop bars in the city is Raised, which is right on the Chicago River. Here you get more than just a stellar city view: the drinks and bites are off the charts, too. The whole place has a cool, modern, industrial feel without being too gray and sterile, with a fire pit for when it starts getting chilly in the fall.

20. …or in a speakeasy

Prohibition may be almost a century in the past, but Chicago still has a robust speakeasy culture that makes a night out with friends even more exciting. From actual working barber shops with a secret door, like Blind Barber , to more mysterious places, like The Drifter , finding these speakeasies feels like an adventure of its own.

21. Check out the beaches on Lake Michigan

Dipping your toes in Lake Michigan is as essential as visiting the Bean, especially if you’re visiting in the summer. There are a few superb beaches to choose from; my favorite is Montrose Beach on the North Side. It’s a lot less glamorous than downtown’s Oak Street Beach, but I like that it’s less crowded. Oak Street is a great choice, though, for first-time visitors to Chicago because of the spectacular skyline view you get as a backdrop to your beach day — just aim to visit early in the morning to avoid the massive crowds.

22. Take a walk through Lincoln Park Zoo

Although the Lincoln Park Zoo is technically open year-round, the best time to visit is during the warmer months. The zoo is completely free to visit, and has hundreds of animal species to see. I don’t usually love zoos, but this one’s open plan and genuine conservation efforts give it a different feel.

Plus, the zoo is just the beginning: you can venture just outside it to the Lincoln Park Conservatory (also free) and explore the variety of plants there. Lincoln Park is also an excellent place to hang out or have a picnic.

23. Bike the 606

The 606 is an elevated bike and walking path that was once an abandoned rail line. Its 2.7 miles connects several Chicago neighborhoods, giving you the ideal bike ride through the city. You can easily rent a Divvy bike at whatever point along the trail you’d like to start your journey, returning it to any station you like when you finish. Divvy also offers full-day passes so you don’t have to worry about counting the hours.

Another great option for getting the most out of the 606 trail is hopping on a bike tour like this one , which includes a large part of the trail. Your guide will be able to show you the best parts along with nearby street art and other stops along the way.

24. Go on a wacky street art tour

Chicago has a vibrant street art culture, with many murals that tell the city’s stories through art. Instead of passively admiring the colorful walls, consider joining a street art tour like this one , which showcases some of the more eclectic murals. This is such a great way to learn about local artists and see some works that are more hidden.

25. Immerse yourself in baseball culture in Wrigleyville

Even if you don’t care about baseball (I certainly don’t), a trip up to Wrigleyville on the North Side is a must-do if you want to get a glimpse into the fascinating world of Chicago baseball. Sure, the city might have two teams, but for the sake of making White Sox fans a little mad, I’ll only mention the Cubs. Can you tell I’m a North Sider?

Walking through Wrigleyville in the summertime is a blast, whether there’s a game going on or not. There are rowdy sports bars, fun barcades (bar/arcades), and restaurants serving up Chicago staples like Italian beef, hot dogs, and deep-dish pizza.

Going to a Cubs game only takes the fun one step further, as you’ll be completely entrenched in the intense atmosphere of Chicago baseball, which is quite the spectacle. Sit back, order a hot dog, and watch the game alongside diehard sports fans.

Pin me for later:

I might have a soft spot for Chicago because it’s my home city, but I think it’s the best in the country. Not only are there so many things to do there, but it’s a cultural hub where people from all over the world bring their unique cultures to share with others in the form of food, art, architecture, music, and more.

If you’re planning a trip to Chicago soon (which you should!), what are you most excited to do?

*Some links in this post are affiliate links for products and services we personally use and love. Any purchase you make through them supports us at no extra cost to you. Thanks so much!

About Emily Becker

Emily Becker is a digital nomad based in Costa Rica. She's been traveling on and off since 2014 and has visited 15 countries—planning to tick many more off her bucket list. In addition to writing for BMTM, she works as a copywriter and project manager.

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Learn how to easily plan your dream trip to the Midwest!

15 Best Tours In Chicago Worth The Money

August 14, 2022 by //  by  Midwest Explored Leave a Comment

Are you wondering which guided tours in Chicago you really must go on? You are in the right place.

In this article, I will walk you through what to see in Chicago and tell you which tours in Chicago are worth the money.

Planning your trip to Chicago last minute?

Make sure to book ahead. Hotels and tours often sell out the closer you get to your trip. Here are our top pics for Chicago!

Top Experiences And Tours In Chicago:

• Chicago River Architecture Cruise (Skip the Ticket Office!)
• Willis TowerSkydeck & The Ledge Ticket (Elevator express entry!)
• Navy Pier Centennial Wheel Ticket (Panoramic views of Chicago!)
• Big Bus Hop on Hop Off Sightseeing Tours (24, 48, or 72-hour options available.)

Hop Hotels In Chicago:

• Eurostars Magnificent Mile (In the heart of Chicago!)
• The Peninsula Chicago (Near museums)
• Club Quarter Hotels Wacker (Overlooking the Chicago River!)
• Hotel Blake (Close to Millennium Park.)

There is so much to see and do in Chicago , It is an amazing city. It’s an innovative, vibrant city that mixes the modern and the past seamlessly. 

The culture, architecture, pizza, and somewhat shady past have all made this place famous and a must-visit Midwest city destination . 

But what if you are short on time and want to make the best of your time here? Well, the best way to make the most out of your time in Chicago is to take some of the Chicago tours on offer. 

Whatever you like there is a tour for it and the experienced guides take the second-guessing out of sightseeing. 

In this list of tours in Chicago, I have chosen some diverse and interesting options for you that I feel will keep most people entertained.

From group tours to private tours, from boats to speakeasies I’ve covered them all. 

So if you want to take the stress out of touring in Chicago then maybe book one of these tours and let someone else guide you. 

Here are the best tours in Chicago I have picked for you. Pull up a chair and let me walk you through an easier way to see the Chicago attractions.

Chicago: 1.5-Hour Romantic Sunset Cruise

This Chicago sunset cruise is perfect if you are looking for romantic Chicago date night ideas .

This Chicago: 1.5-Hour Romantic Sunset Cruise is a perfect way to spend some time with your significant other.

You start your sunset cruise on the Chicago River at Michigan Avenue then make your way along the main branch of the river towards Lake Michigan.

The vessel then goes through the locks and cruises along  Lake Michigan. 

there are so many places to stay in Chicago along Lake Michigan.

As the sun sets you are treated to the most beautiful view of the Chicago skyline with that beautiful sunset glow.

You can also purchase snacks and drinks on board and I don’t know about you but sunset and champagne sound perfect. 

There is a short narration at the beginning of the cruise but most of the cruise is just about admiring the view no narration is needed. 

The cruise last 1 ½ hours and you will see many Chicago attractions. You can sit on the open deck or inside whichever you prefer but the deck has to there best right?

This really is one of the best Chicago tours for couples.  

Book : Chicago: 1.5-Hour Romantic Sunset Cruise

Chicago River: 1.5-Hour Guided Architecture Cruise

If you are looking for a Chicago architectural boat tour then this Chicago River: 1.5-Hour Guided Architecture Cruise will be perfect for you.

If you have come to Chicago in search of architectural Chicago sights then you will love this tour.

Here you can experience the Architecture from the top deck or inside as you travel along the main River and its north and south branches.

Things you will see include Wrigley Building and the Tribune Tower, the imposing art deco Merchandise Mart, and mid-century skyscrapers like the Mies Van der Rohe AMA Building among others. 

The guides are experienced and the narration gives you all the information you need. The tour lasts 75 minutes and if you are short of time and want to see a lot this is the boat ride in Chicago for you. 

Book Here: Chicago River: 1.5-Hour Guided Architecture Cruise

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

There are so many great restaurants in Chicago it can be hard to know where to start. This Chicago Food Tasting: 2.5-Hour Guided Walking Tour is a great way to get a taste of Chicago.

I don’t know about you but everywhere I go I want to do a food tour, I feel like food tells you so much about a city, and this Chicago food tour is no exception. 

This 2 ½ hour walk around downtown introduces you to some of the city’s top sites. You will get to enjoy deep-dish pizza, Italian pastries, a Chicago-style hot dog, and a classic Italian beef sandwich. 

You will also see some of Chicago’s historic buildings along the way which course will be pointed out to you. 

The pace is leisurely, the food great, and some of the places iconic what more could you want? 

Book Here : Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Chicago: 45-Minute Private Helicopter Flight for 1-3 People

If you are looking for Helicopter tours in Chicago then this one is perfect. Chicago: 45-Minute Private Helicopter Flight for 1-3 People shows you the city from a different perspective.

You will see all of the important Chicago sights from a vantage point most others don’t get to enjoy. 

The McCormick Place, Soldiers Field, Wrigley Field, Willis Tower, the John Hancock Building, Navy Pier, and Lake Michigan are all highlights.

You depart from Schaumburg Regional Airport and the flight last 45 minutes. It’s a private flight with a maximum of three passengers.

The commentary is perfect, and in summer if you want you can fly with the doors off.

Book Here: Chicago: 45-Minute Private Helicopter Flight for 1-3 People

Chicago: Treasures Of The Golden Age Walking Tour

If your idea of getting to know the city is more from the ground than up in the air then how about a Chicago walking tour?

Chicago: Treasures of the Golden Age Walking Tour covers the most significant Chicago attractions.

The guides are trained by the Chicago Architecture Center and the tour focus on great cultural buildings from the late 19th and early 20th centuries.

So expect to see lots of Beaux Arts, neo-Georgian and neo-Gothic.

And you will get to go inside some of the buildings too. Highlights include Chicago Cultural Center, home to the world’s largest Tiffany dome.

And the iconic Marshall Field department store, now Macy’s on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

This just seems a beautiful way to see the city and is one of the best tours in Chicago.

Book Here: Chicago: Treasures of the Golden Age Walking Tour

Chicago: Mob and Crime Bus Tour

If you are looking for a Chicago gangster tour the Chicago: Mob and Crime Bus Tour will be perfect for you.

When in Chicago this just has to be done right? This tour in Chicago takes you into the underworld of criminals and gangsters all in the confines of a luxury bus. 

On this tour, you will learn about some of the world’s most famous criminals, mobsters, and gangsters and see some of the famous Chicago crime scenes. 

This interactive tour will teach you all about Al Capone, the Untouchables, and the Chicago Mob.

Also John Dillinger, Terrible Tommy O’Connor, H. H. Holmes, the Chicago Black Sox, Leopold, Loeb, bank heists, Cap George Streeter, and more.

If you have an interest in all things crime, murder, and the gangster underworld you are just going to love this Chicago activity.  

Book : Chicago: Mob and Crime Bus Tour

Chicago: Windy City Ghosts Haunted Walking Tour

And now we move from gangsters to ghosts. This Chicago ghost tour goes through Northside Chicago and visits some of the city’s most haunted locations.

If you love a scare Chicago: Windy City Ghosts Haunted Walking Tour is for you.

The tour is laced with tales of spirits, people long forgotten and ghosts still making their presence known.

Will you see the Victorian woman in white who is seen in the bathroom mirrors at Lincoln Park Zoo? 

On the standard tour, you visit eight locations but this can be expanded to visit 12. Personally, I’d opt for all 12 but I love a good ghost story. 

This is the best tour in Chicago if you love all things scary.

Book: Chicago: Windy City Ghosts Haunted Walking Tour   

Chicago: City Minibus Tour With Optional Architecture Cruise

This is a great sightseeing Chicago bus tour if you prefer to see the city in comfort.

Chicago: City Minibus Tour with Optional Architecture Cruise also you to see the sights of Chicago in comfort.

You begin in the heart of downtown Chicago and go from there. There are too many stops to mention on this tour but let’s just say it’s a lot.

You will see the world’s first skyscrapers, see a beautiful lobby designed by Frank Lloyd Wright and visit the fancy Gold Coast nightlife area where the original Playboy Mansion is. 

This tour of Chicago lasts a couple of hours and there is an option to extend with a 75-minute cruise of all three branches of the Chicago River.

This is one of the best tours if you are not sure what to see in Chicago as it shows you so much.

Book: Chicago: City Minibus Tour with Optional Architecture Cruise

Chicago: Fireworks Cruise With Lake Or River Viewing Options

If you are after a Chicago boat tour/river cruise then Chicago: Fireworks Cruise with Lake or River Viewing Options offers something a little bit different.

This boat cruise allows you to see the amazing fireworks display off Navy Pier from the boat. 

There is a short narration on some history and architecture at the beginning of the cruise then it’s all about fireworks, which you can watch outside on the deck or inside. 

There is a short and long version of this boat ride in Chicago. The longer one lasts 2 ½ hours the shorter about an hour so choose which one feels best for you.

In the longer version, you go through the locks and into Lake Michigan for an incredible view of the city. 

Book Here: Chicago: Fireworks Cruise with Lake or River Viewing Options

Chicago: History, Culture And Architecture Walking Tour

If you are looking for a Chicago architectural tour then the Chicago: History, Culture and Architecture Walking Tour is perfect for you. This is a great way to go sightseeing in Chicago.

The tour starts under the dazzling marquee of the Chicago Theater and heads off into the city from there. 

You will get to walk the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. 

On this tour, you go inside City Hall sample some Chicago-style popcorn, stroll along the Chicago Riverwalk, and much much more.

 Notable sites are the Wrigley Building and the incredible Chicago Tribune building, Millennium Park, and many more. 

Oh, and you also go chocolate tasting if you needed any more convincing. It’s a perfect enhancement to your Chicago Visit.

Book: Chicago: History, Culture and Architecture Walking Tour

Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

For the ultimate in sightseeing, the hop-on-hop-off Chicago is a perfect way to tour Chicago.

Chicago: Big Bus Hop-on Hop-off Sightseeing Tour is a double-decker bus that gives you a great vantage point to experience all of the city’s impressive landmarks. 

Sights the bus takes in include the John Hancock Center, the Willis Tower, the Wrigley Building, and the famous Magnificent MileMichigan Avenue Bridge over the Chicago River.

You can hop on and off as many times as you want so you can explore the sights at your own pace.

Tickets last for 24/48 hours so It’s a great way to help you get around the city to see everything. This is touring in Chicago at its best.

Book: Chicago: Big Bus Hop-on Hop-off Sightseeing Tour

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

f you want to be treated like a star for the evening on your Chicago visit then how about a private speakeasy tour? 

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tou r is a real delight for those that want to feel a little bit special.

You visit the speakeasies that have been open since the Prohibition Era in the 1920s many still as original as the day they were built.

You enter via secret entrances and enjoy the same cocktails the infamous gangsters in the area loved. 

If you love the 1920s and all its history then this tour of Chicago is for you.

You travel around with a young professional guide who advises you on the best drinks and you are chauffeured to the places in luxury transportation. 

If you wondered what it feels like to be a famous gangster this is your time. 

Book: Chicago: 3-Hour Private Speakeasy Cocktail VIP Tou r

Chicago Underground Donut Tour In Chicago

I know a donut tour might seem a little odd but honestly, the Chicago Underground Donut Tour is perfect for a group of friends.

The tour is in the downtown area and you get to try donuts from Stan’s Donuts, Do-Rite Donuts, and Firecakes Donuts, which are true donut institutions in this area, 

The tour takes two hours and if you don’t know anything about donuts yet you will by the end of this tour, you also be pretty full too.  

So if you are after something a little different then this might be perfect for you. This is a great Chicago activity.

Book Here: Chicago Underground Donut Tour

Amazing Lakefront Segway Tours Of Chicago

Fancy sightseeing in Chicago in a relatively new form of transport then how about a Segway?

On the Amazing Lakefront Segway Tour of Chicago , you will be gliding around the streets and parks of Chicago without a care in the world. 

You will uncover quirky facts about the city and have fun at the same time.

The tour starts with a training session before you make your way around Millennium Park and continue to Grant Park to stop and admire the famous Buckingham Fountain

You also ride to Museum Campus where you get a great view of the Chicago skyline and beautiful lakefront. This is a great fun way to see the city and if you have teens they will love this. 

This is one of the best tours in Chicago and a great way to see the sights of Chicago and experience some of the breweries in Chicago.

Book Here: Amazing Lakefront Segway Tour of Chicago

Chicago: Night Tour With Willis Tower Entry & Skyline Cruise Is One Of The Best Tours In Chicago

For the ultimate tour, you might what to try the Chicago: Night Tour with Willis Tower Entry & Skyline Cruise .

You get to see the Windy City’s most prominent sites, watch the Buckingham Fountain night light show, enjoy a Chicago skyline cruise, and go to the top of the iconic Willis Tower.

You really do get everything with this tour. The first stop is the Willis Tower, the tallest building in the Western Hemisphere.

You get to go to the top and take in the view. You also see over 40 iconic landmarks on this cruise. This is one of the coolest things to do in Chicago at night!

Then you go on a night skyline cruise and see the city all lit up. After that, you get to watch the spectacular light and music display at Buckingham Fountain.

It’s the perfect Chicago tour if you are short on time.

Book: Chicago: Night Tour with Willis Tower Entry & Skyline Cruise .

Packing List For Doing Tours In Chicago

If you are searching, here are some  tips on how to pack lightly when packing to take tours in Chicago.

A  concealed travel pouch  may be one of the most important items you bring along when touring Chicago.

It is always important to protect your personal information. Identity thieves are everywhere.

This  unisex RFID blocking concealed travel pouch is  lightweight and comes in several colors. It has lots of organization to give you peace of mind.

If you have a pouch already that does not come with the RFID protection, as I do, these  RFID  sleeves are  the perfect solution.

This configuration comes with enough credit card sleeves that the entire family would be protected. They are slim too, so they will easily fit into your pouch or wallet.

If you are planning on taking a lot of pictures with your phone you will definitely want to consider an  external charging battery . This  Anker high-speed phone charging battery  is  the exact one  I carry with me on all of my trips.

It can be used on a variety of phones, not just an iPhone like I have. And wow is it fast!

I like that it holds its charging capabilities for several uses so I do not have to worry about it while out and about, and if I forget to recharge it at night, it will still be good to go the next day.

My daughter gifted me with this  FugeTek selfie stick and tripod   setup for my birthday. I absolutely love it! It is made of lightweight aluminum and is so easy to use.

It has Bluetooth connectivity and is a breeze to use for taking selfies with family and friends when taking Chicago tours.

Hydration is so important when traveling. You want to remain hydrated throughout your travels to support your immune system which in turn will be stronger to fight off any germs you will encounter during your travels.

You will want to bring your own  refillable water bottle  with you.

I never leave home on a trip without my  Bobble filtration bottle .  The 18.5-ounce size is perfect for hiking and it fits nicely in the pocket of a backpack.

When filled with water, it is not too heavy to carry. And the charcoal filter ensures fresh clean water whenever you fill the Bobble.

Perhaps you are traveling a long distance and packing space is a premium in your suitcase, or in your car.

Then this  set of collapsible silicone foldable water bottles  would work well for you. Would not take up much space at all.

You will want a  backpack or daypack  with you to store snacks, your water bottle, phone, extra clothes, etc.. then this   foldable water-resistant backpack   would be great.

As you can see when it comes to tours in Chicago there are so many to choose from. Tours are a great way to see the Chicago sights. And a perfect way to enhance a weekend in Chicago!

And if you want to start your day right, check out some of the best places for breakfast in Chicago!

Whichever of these Chicago tours you choose I hope you have a great time and please come back and tell me all about it.

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Chicago All Day Tours

• Chicago Black Heritage Tours

South Side Tours

North side tours.

• Testimonials
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• Chicago, IL

Personal Neighborhood Tours

Chicago, il has 77 distinct neighborhoods. we will show you the real chicago., personal neighborhood tours.

This is not a bus tour, our tours are done in a luxary van. From 2-11 people or groups or more, we provide large luxury vans offering 4 different tours of Chicago. For large groups, contact us below for arrangements. Pricing is according to the size of the group. Book a tour with our personal neighborhood tour guide today. We can't wait to show you all that this city has to offer.

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund. For a full refund, you must cancel at least 24 hours before the experience's start time. If you cancel less than 24 hours before the experience's start time, the amount you paid will not be refunded. Any changes made less than 24 hours before the experience's start time will not be accepted. Cut-off times are based on the experience's local time. Due to safety and availability we require only a 2 person minimum for all tours!

We Offer 4 Distinct Tours Of Chicago,

Chicago american heritage tour, get blown away by the windy city.

• Chicago guided tours
• Historic tours of Chicago
• South Side tours
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Take in the Sights and Beauty of Chicago

Explore the city with a professional chicago tour guide, why choose chicago personal neighborhood tour.

• We always give our clients a memorable experience
• We provide transportation to and from the airport
• We offer the highest level of customer service

See the sights with an expert

• Sit back and relax, rather than navigate traffic by yourself
• Ask questions about landmarks that stood out to you
• Get first-hand knowledge from a native Chicagoan
• See all of Chicago in just one trip

This tour far exceeded our expectations. First of all, let me start with our tour guide (Steve). Steve was the ABSOLUTE BEST!!! Our visit was during the Christmas holiday not to mention it was during the Arctic blast where it was the coldest days Chicago hadn't experienced in years. If it wasn't for Steve providing us with multiple tours, we would have been stuck in our hotel with nothing to do. I can positively say that we wouldn't have gotten this experience with no other tour or tour guide like Steve provided to us. My friend and I had no idea Chicago had so much history until Steve enlightened us on all aspects. I just cannot express my gratitude for Steve. He loves his city and is very passionate and knowledgeable regarding everything about Chicago. If your going to Chicago, this is A MUST tour that you need to book. Definitely, make sure you request Steve...

Excellent tour. Steve gives you everything you n Ed to know about Chicago. Enjoyed the history of this great city.

Steve was an excellent tour guide very knowledgeable very prepared and on time, great personality, easy to communicate with and went out of his way to make the trip an enjoyable one. Steve knew of all current and past events, and gave us a detailed history of all of Chicago , Lunch was fabulous, it was just an absolute pleasure, Steve made the entire trip enjoyable will definitely be back!!!

Thank you Steve for my excellent tour. I felt l learnt so much about the neighbourhood and African American history through your knowledgeable commentary. Also l thank your company for allowing me to have a solo tour (many companies have a two person minimum which means l often miss out!!). Thanks again Steve, l enjoyed my private tour!, your company and our conversation.

pamelacoburn

Our tour guide, Steve was excellent. He was able to accommodate a larger group than normal who were mostly seniors. His knowledge of the history of Chicago and African American experience in the city was extremely impressive. The soul food buffet dinner at Pearls made for a very enjoyable time.

We had an amazing experience from the beginning. Steve called the day before to verify pick up location and communicated often. We didn't feel rushed or like tourists. I definitely see Chicago in a different light. We felt safe and learned so much. Definitely worth the time and money. The food was great and the hospitality from the driver (Steve) is unmatched. Book this tour!

Chicago has so much history to offer. It was great to have a tour catered to places and history my husband and I wanted to see and learn about. Our tour guide, Steve, was punctual, insightful and knowledgeable about his city. There were plenty of photo opportunities and even allowance to add more time on to the tour if you desired. The added bonus of a meal was wonderful. The food at Pearl's Place was very flavorful (great soul food and plentiful on the portions). If you are looking for a generic tour with an automated or scripted guide this is not the one. However, if you want to be interactive, engaged, and have a little trivia pursuit this is the tour for you, and Steve was great!

Absolutely wonderful! Tour guide Steve went out his way to assure we had an wonderful experience. We learn so much about Chicago on this one tour than if we would have on our own. Thank you Steve

Wow!! This tour made me feel like I had gone back in time. I'm not from Chicago, but i made a lot of connections with the scenery. Especially seeing where people, I had heard of from the past, their beginnings (home address). The driver, Steve, made the tour worth while.

ARBARAGENE_M

We enjoyed the entire tour. Steve has a vast knowledge of Chicago as well as African American history. He is pleasant and engaging tour guide. I highly recommend this tour.

Call Us Today to Schedule a Black History Month Tour!

Discover Chicago's Secrets with Magnifico Tours

At Magnifico Tours, we’ve reimagined Chicago exploration, intertwining the city’s mysteries and tales into our adventures. While our specialty lies in crafting detective intrigue within our Chicago Walking Tours, we embrace the rich tapestry that is Chicago’s history, from its notorious gangsters to its spectral legends, and from its architectural marvels to its vibrant cultural districts like Old Town.

The Chicago Murder Mystery Tour invites you to step into a detective’s shoes, solving mysteries as you navigate the city’s landmarks. And alongside the sleuthing adventure, our Private Chicago Magnifico Tour offers a unique Spanish-language journey through Chicago’s cultural wonders.

With Magnifico, every tour is a story, every moment a clue in the grand narrative of Chicago.

Our Chicago Walking Tours

The Chicago Murder Mystery Tour

Embark on a thrilling journey through Chicago’s Gold Coast with our Chicago Walking Tours. Not only will you delve into the city’s mysteries and legends from Al Capone to the Playboy Mansion. A must-experience for every true-crime aficionado.

Schedule: Daily

Start Time: 2 PM, 4:30 PM, 7 PM

Language: English

Duration: 2 Hours

View Highlights

The Private Chicago Magnifico Tour

Embark on a 2-hour journey through Chicago’s vibrant history with our expert guides. Dive into tales of Al Capone, architectural wonders, and our city’s rich Latin culture. Spoiler Alert: You’ll also get to know where NOT get Deep Dish Pizza!

Start Time: Customizable

Language: Spanish

Duration: Customizable

Testimonials

Our guests often find themselves immersed in the rich and varied tales of Chicago, exploring narratives that span from the spectral to the criminal, from the architectural to the historical. Whether it’s the allure of Chicago Gangster Tours, the spine-chilling tales reminiscent of Chicago Ghost Tours, or the architectural marvels that might be explored in a Chicago Architecture Tour, our adventures touch upon diverse threads of stories that make up the fabric of the city.

Mi parte favorita fueron las historias .

Mi parte favorita fueron las historias..

Muchas Gracias!

It’s the highlight of our trip to Chicago .

It’s the highlight of our trip to chicago..

This tour was amazing .

This tour was amazing..

Excellent fun!

Why You Should Go For Magnifico Tours

Our tours, while specializing in mystery and detective-themed experiences, also provide glimpses into other fascinating aspects of Chicago. Whether it’s the notorious past explored in Chicago Gangster Tours, the spectral stories you might find in Chicago Haunted Tours, or the architectural wonders celebrated in Chicago Architecture Tours, Magnifico ensures a rich and varied exploration of the city

Expert Guides

Our guides are Chicago enthusiasts and history buffs, blending historical knowledge with local insight.

Immersive Tours

Immerse yourself in an intriguing experience blending historical facts with captivating storytelling.

Exclusive Access

Our tours enter places not accessible to the general public so you can experience gems of Chicago.

Customizable

Personalize your journey! Tailor the tour to fit your unique interests and comfort level.

Inclusive Fun

Everyone – families, couples, friends, and solo travelers – is welcome for a memorable experience.

All-Weather

Regardless of rain or shine, our tours proceed. Plus, we offer easy rescheduling options.

Whether you’re exploring the city on foot with our Chicago Walking Tours, delving into the city’s notorious criminal past akin to Chicago Gangster Tours, or exploring the spectral stories similar to those in Chicago Ghost Tours, we ensure your adventures with Magnifico Tours are seamless and memorable. Find answers to common queries below, and prepare to step into the multifaceted stories of Chicago with us.

The closest parking garage to the Murder Mystery tour is located at 110 E Pearson St. And for the Magnifico Chicago Private Tour, the closest parking can be found at 505 N Michigan Ave.

Yes, it is a walking experience! The Chicago Murder Mystery is an interactive game that takes you through the city, revealing thrilling stories and showing you sites as you also solve a crime. The crime-solving bit is an interactive experience; if you don’t feel like taking part, you can opt out!

No worries, you are not obligated to perform. We often have families come where some wish to participate and others play as encouraging audience members. In the event where everyone is shy and less interested in playing, your tour can take on a more typical walking tour experience.

Our team is 100% responsive within a 24 hour period, and can be best reached by email [email protected] and Phone/Text/Whatsapp at 872-310-7645. Tickets are 100% refundable until 24 hours before a tour. If you need to cancel within 24 hours of the tour, you may reschedule onto any future tour. Again, please reach out by email or phone/text/Whatsapp.

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The Great Literary Tour of Chicago

Arts, Culture & History

3 Days 60 Miles

Chicago, Oak Park

Explore the city’s literary legends

Bookworms can take in the rich culture of Chicago’s literary history. Take the Devil in the White City Tour, inspired by Erik Larson’s best seller. Pay tribute to Chicago’s brightest authors at the very first crowd-sourced exhibition, Chicago Authored. Head to Oak Park to Ernest Hemingway’s Birthplace Museum and see where the author’s roots began. Extend your trip outside the city for experiences surrounding other writers like Carl Sandburg in Galesburg, Ray Bradbury in Waukegan and many more.

Your literary-themed adventure begins at the American Writers Museum in Chicago - the only national museum dedicated to American writers and their works featuring informative, interactive exhibits honoring notable U.S. writers throughout history. Just blocks away, browse through the After-Words Bookstore offering new and used books featuring fiction, literature, poetry and children’s books. Next, stroll by the nearby Art Institute of Chicago to take a picture with the iconic Lions that guard the building. The Art Institute of Chicago is where the main character, Russell Stone, works in the popular Richard Powers’ novel, Generosity: An Enchantment . 

Nearby Grant Park – a sprawling open space featuring picturesque skyline views and known as “Chicago’s Front Yard” – is home to Buckingham Fountain and was featured in the popular novel, The Time Traveler’s Wife . Not far from Grant Park, just across Chicago’s famous Michigan Avenue , you can get lost for hours inside the Harold Washington Library Center , the Chicago Public Library’s main branch. Inside the building, discover the Winter Garden that features incredible natural light that makes for a great photo op. Next, head north to stop for lunch at Beatnik on the River , known for its chic, Bohemian decor along with progressive, globetrotting dishes and cocktails. 

Continue north across the Chicago River and take in the city’s incredible architecture as you make your way to the Poetry Foundation in the River North area. The first space in Chicago dedicated solely to the art of poetry, the  Poetry Foundation is a 30,000-volume poetry library that features an exhibition gallery and performance space for live poetry readings and public events. Head west across the Chicago River to Semicolon Bookstore in the nearby Chicago’s River West area. Semicolon is Chicago’s only Black and woman-owned bookstore and gallery that focuses on both community and literacy, with an emphasis on supporting Black book-buying and bookselling. 

The day would be incomplete without a literary-themed dinner at one of Chicago’s many quaint restaurants dedicated to creating the feeling of wanting to curl up with a good book. At Wilde Bar & Restaurant in the Lakeview area, named after Oscar Wilde, you can enjoy an extensive beer list and Irish pub food under a stained glass ceiling dome, along with a charming library nook and two cozy fireplaces. If you plan to stay around the River North area, the Library at Gilt Bar is a low-lit basement bar offering red-velvet booths along shelves of vintage books, perfect for a romantic dinner for two. 

Chicago offers numerous hotels to complete a literary-themed getaway, like Freehand Chicago , which boasts a gathering room decorated with one-of-a-kind Mid-century modern furnishings and decor along with a well-curated selection of books on Midwestern art, design and architecture. Stay in the hip Publishing House Bed and Breakfast - an industrial-style boutique B&B situated inside a former publishing house. Along the city’s famous Magnificent Mile,  you can stay at the Four Seasons Hotel - Chicago , where a stylish “Author Suite” sits on the 46th floor offering sweeping panoramic views of Lake Michigan. The suite includes an extensive library filled with signed works by Stephen King, Margaret Thatcher, Oliver Stone and Anne Rice – all former guests of the hotel!

Kick off your second day aboard Weird Chicago’s Devil in the White City Tour and experience the dark history of the infamous serial killer, H.H. Holmes, and the remains of the 1893 World’s Fair, like the Museum of Science and Industry . Next, discover rare books and manuscripts at the The Newberry Library - a stately five-story research library that served as the main character’s place of employment in the novel The Time Traveler’s Wife .

Your second day calls for branching out and discovering more Chicago neighborhoods. Head north to Lincoln Park to discover the Chicago History Museum – Chicago Authored exhibit highlighting authors that helped define and navigate the character and complexity of Chicago as a whole. Stop for lunch at The Red Lion Pub , also in Lincoln Park featuring roaring fireplaces and shelves adorning an impressive collection of British literature. Next, discover Oz Park , an entire park dedicated to The Wizard of Oz, a book that was written by Chicago reporter L. Frank Baum. Oz Park brings the book's characters to life as statues are peppered throughout the park. Continue north and grab a bite to eat or drink at The Monkey’s Paw in Lincoln Park, a gastropub that’s reminiscent of a high-school English classroom and named after the famous short story of the same name by W.W. Jacobs. Head northeast to the Northalsted neighborhood home to Unabridged Bookstore - the city’s go-to-bookstore for LGBTQ literature. 

Make your way even further north to the Andersonville and Edgewater areas. Lady Gregory’s is another literary-themed gastropub to discover in Andersonville, featuring a library and over 300 whiskeys to choose from. Edgewater offers a couple unique bookstores, Women & Children First – a feminist and kid-focused book shop, and Unchartered Books – a rare and used bookstore, along with the City Lit Theater Company ,  dedicated to the vitality and accessibility of the literary imagination with concert readings and full-stage productions of adaptations of literary material, scripted plays and more. 

If you visit in September, be sure to stop by the annual Printers Row Literary Fest , a two-day festival featuring carefully selected offerings from over 100 booksellers – everything from the tattered to the rare to ‘hot off the press,’ newly published works.

On your last day, head to the charming town of Oak Park , a half hour drive west from Chicago. Start with a delicious brunch at Hemmingway’s Bistro which offers classic French fare, an extensive wine list and Sunday brunch buffet with live jazz music. Discover more Hemingway at the Ernest Hemingway Birthplace Home and Museum - the ideal place to explore the roots of the author’s life and work. The history in Oak Park doesn’t stop there though. You can get an in depth look into the life of famed architect, Frank Lloyd Wright , at his Home & Studio   one of the stops along the Illinois’ Frank Lloyd Wright Trail that highlights 13 architectural gems he built around the state. Make sure to also plan a visit to Edgar Rice Burroughs ’ former Oak Park home where he wrote 11 novels including  his most famous book, Tarzan of the Apes . Learn more about well-known Oak Park writers, architects, artists, scientists, social activists and more at the Oak Park River Forest Museum and Oak Park Public Library .

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Chicago-My Kind of Town

Chicago, aka the "Windy City", remains one of the premier tourist destinations in the Midwest. Over 45 million people visit Chicago every year to discover everything from world-renowned museums, jaw-dropping architecture, delicious food, and unbeatable shopping. We are staying in Chicago for 2 nights where you can enjoy free time or join us for some optional meals and attractions.

• Detailed Overview
• Tour Itinerary
• Pick-up Points
• Departure Dates

Studebaker Museum

Guided Tour of Notre Dame Campus

Chicago Highlights Tour

Free Time in Chicago

Willis Tower

Optional Meals and Touring Available

8 Meals Included

Motorcoach Transportation

Hotel Accomodations

Requires Extended Amounts of Walking

Today we will begin our westward journey. With stops for rest and lunch enroute, we will arrive in Westlake, OH, the location of our lodging this evening. Dinner will be on our own.

After breakfast we will head to South Bend, IN. After an included lunch, we will visit the Studebaker National Museum where you will be able to explore the collection of approximately 120 vehicles including automobiles, wagons, carriages, and military vehicles at your own pace. We will then depart for Notre Dame Campus for a guided walking tour which highlights the Grotto, Main Building, and Hesburgh Library. We will then check-in to our lodging and enjoy an included dinner at a local restaurant.

Following breakfast we will travel to Chicago where we will meet our guide for a city highlights tour including the Magnificent Mile and Chicago's "loop". We will also have a walking tour of Millennium Park. This must-see attraction in the heart of downtown Chicago features one of the most famous icons The Cloud Gate aka "The Bean". Next, we will visit the Navy Pier for lunch on our own and free time. Afterwards, we will check-in to our Chicago accommodations and enjoy dinner on our own at one of the local restaurants. Optional Evening Activity - $60 per person additional Chicago River Cruise. Witness breathtaking views of the magnificent skyline and up-close perspective from the Chicago River with live narration highlighting Chicago's rich history and architectural heritage.

After breakfast, today is yours to explore Chicago's attractions on your own or join us for one of our optional excursions. You are able to do all optional activities if desired. Optional Morning Activity - $60 per person additional Chicago Botanic Garden. Experience over 300 acres of vibrant landscapes on a guided tram tour. As part of our visit, you will also have the opportunity to explore the popular seasonal attractions on your own. Optional Evening Activity- $100 per person additional Chicago's Original Gangster Tour & Dinner. Join us for a very entertaining but unforgettable Chicago crime tour. Hear about the crimes and activities that were happening in Chicago during the 1920s and 1930s. Dinner will be included at a local restaurant.

This morning, after breakfast, we will visit the tallest building in Chicago, Willis Tower. We will travel by elevator to the 103rd floor to The Ledge, a glass balcony extending four feet from the skyscraper. Enjoy spectacular views spanning up to 50 miles and four states. Lunch will be a famous authentic "Chicago Style" deep dish pizza. This afternoon we will begin our trek home with an overnight stay in Maumee, OH. Dinner will be on our own this evening.

Today after breakfast at the hotel, we will travel back home. With stops for rest and lunch enroute, arrival home is scheduled for early evening.

Please note

Our intention is to run each tour as originally planned and published. However, if deemed necessary to do so, Perkiomen Tours reserves the right to make changes to tour components, schedules, or itineraries without prior notification. Tips for Perkiomen motorcoach drivers and tour escorts are not included in the price of this tour. We feel that these gratuities should be extended on an individual basis and dictated by the level of service provided. Motorcoach seating is assigned at the time of reservation but cannot be guaranteed. Although we do our best to keep each traveler in the seat assigned at the time of reservation, there are times that it is necessary to move seat locations. Please be sure to verify your final seat number(s) with your driver at the time of boarding. Historically, daily seat rotation was practiced on most multi-day tours. We have suspended this practice for a period of time. Seat rotation will be explained by your driver or tour escort if reinstated. Perkiomen Tours recommends that you consider purchasing Travel Insurance for your tour. Travel Insurance is purchased directly by you from a third-party of your choice. One option is Travel Safe Insurance. You can purchase insurance directly from Travel Safe through our website. www.perkiomentours.com. To fully participate in this tour may require extended amounts of walking. There may be steps, inclines, uneven surfaces or extended periods of standing. Participants with physical limitations should take this into consideration.

CB=Continental Breakfast, B=Full Breakfast, L=Lunch, D=Dinner

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9 Great Chicago Architecture Tours

I f you're looking for the best Chicago architecture tours, you've found them here! As a local who has explored these tours on weekends, during staycations, or while showing visiting friends around Chicago, I can honestly say that this list shares the most unique and fun experiences.

The city has great options including the best architectural boat tours, helicopter tours, walking tours, and more.

If you have limited hours, take the Hop On/Hop Off bus tour in Chicago or visit the top Chicago attractions to get the most out of a short amount of time.

Architecture Tours You Should Try in Chicago

Chicago architecture cruise.

Check rates for Chicago Architecture Cruise

If you love touring on water, then this cruise is for you. I've taken this cruise several times while showing friends the city and they loved it too.

On this cruise, you will ride the Chicago River and see the city's famous architecture. You'll see the impressive flat skyline including over 40 famous buildings such as Navy Pier, the Wrigley Building, and the John Hancock Building with audio narratives. The tour covers all three branches of the Chicago River.

Navy Pier Centennial Wheel Regular & Express

Check rates at Navy Pier Centennial Wheel

This is one of my favorite ways to see the city and the Chicago skyline. You circle only once, but the ride is super slow, and you'll have some great photo ops when you get to the top.

Navy Pier is among the most visited destinations in the world. It offers beautiful views from the wheel, and it's a must-do when in the area! Located right on the pier, you have spectacular views of the city's skyline, architecture, and waterfront.

45-Minute Private Helicopter Flight

Check rates at 45-Minute Private Helicopter Flight

I was scheduled to go on this flight but it was canceled due to bad weather. At least they are good at following safety protocol. Too bad that I missed this amazing experience by helicopter. From what I hear, you will get the best views of touring Chicago architecture, and the experience of flying amongst the clouds. 

Willis Tower Skydeck and The Ledge

Check rates for Willis Tower Skydeck and The Ledge

Having been on the Skydeck a couple of times, it never disappoints. What I didn't like much was that there is a limited time that you have to stand in the box. But if there were no supervision, the line would be from the street.

But here, you will have some of the most breathtaking views of Lake Michigan. You'll also see why home is to beautiful parks and cultural attractions such as the Adler Planetarium in Millennium and the Shedd Aquarium in Grant Park.

Look north to see Chicago's iconic skyscrapers and landmarks from Lincoln Park to the world-famous Wrigley Field.

Night Tour with Willis Tower Entry & Skyline Cruise

Check rates at Night Tour with Willis Tower Entry & Skyline Cruise

This tour is a wonderful way to spend the evening while touring in Chicago. You'll immerse yourself in one of the tallest architectural buildings in Chicago along with a Chicago boat tour. 

Experience the Windy City’s most popular attractions on this overnight tour. Watch the night light show of Buckingham Fountain. Cruise along the Chicago skyline and climb to the top of the iconic Willis Tower.

Big Bus Panoramic Sunset Tour with Live Guide

Check rates at Big Bus Open-Top Panoramic Night Tour

If this is your first visit to this city, this is a great way to tour Chicago , Illinois and how it shines at night. There is so much to see on both sides of the bus since the architecture of Chicago is interesting

Experience the stunning skyscrapers of Windy City that light up at night. Take a panoramic nighttime tour from the Magnificent Mile to Michigan Avenue past the Chicago Theater and Buckingham Fountain.

Chicago History, Culture, and Architecture Walking Tour

Check rates at Chicago History, Culture, and Architecture Walking Tour

This is a great way to hear about Chicago's history and architecture. Take a private stroll or share walks with family or friends for this architecture tour. You can see old and new architecture, try delicious local treats, see beautiful boats tour the river. 

Chicago Architecture Center Exhibit Admission

Check rates at Chicago Architecture Center Exhibit

The Chicago Architecture Center or CAC is located at the south end of Magnificent Rock near Michigan Walker Intersection. You'll discover super-sized models of architecture from around the world.

The vouchers give you access to two floors of imaginative exhibitions at the city's newest cultural venue.

Chicago Art Deco Skyscrapers Walking Tour

Check rates at Chicago Art Deco Skyscrapers Walking

The luxurious materials and geometric decorations of Art Deco represent the opulence and optimism of the decadent 20s. Visit some of the city's most beautiful architecture and learn about the history and characteristics of this modern decorative style.

Final Thoughts on the Best Chicago Architecture Tours

These are the best ways to tour Chicago architecture and see all the unmissable attractions. I've taken every single one of these tours, including ones not mentioned and found them worth the money.

I enjoyed seeing the towering skyscrapers and iconic landmarks. The tours offer a fascinating glimpse into the architectural history of the Chicago. Not to mention, it's nice to play tourist in my own back yard.

As a visitor, be sure to plan your tour in advance and consider factors such as weather and time of day to make the most of your experience. Don't forget your camera to capture the stunning views along the way.

Whether you're an architecture enthusiast or simply looking to appreciate the city's remarkable skyline, a Chicago architecture tour is a must-do activity. The buildings are inspiring structures and some are a marvel of innovative designs that have shaped this iconic city.

Whether you go on water, in the air, or on foot , book your tour today and embark on a journey through Chicago's architectural wonders.

As  full-time digital nomads , we’re travel experts . Follow us for travel tips!

Our Offbeat Life contains affiliate links & participates in the Amazon Services LLC Associates Program & other affiliate programs. If you buy something using an Amazon or other link, we may receive a commission at no extra cost to you. See our Disclosure for more details.

10 Best Chicago Private Tours to Book in 2024

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Have you been wondering about Chicago private tours? You’ve come to the right place!

Chicago is a city with so much to offer and exploration of the Windy City through private tours is an incredible way to experience its unique and vibrant culture.

I lived in Chicago with my family for over 16 years and had the chance to take and give private tours showing off what makes the town so special. Of all the places we’ve traveled as a digital nomad family, Chicago is still one of my favorite cities. I know all of the top spots for any great Chicago private tour: from Buckingham Fountain in Grant Park all the way up to the John Hancock Observatory, you’ll get to see many of Chicago’s must-see attractions on these curated tours.

Private tours offer a chance to hear the stories behind some of Chicago’s iconic architecture or get a taste of local cuisine at a restaurant off the beaten path. There are plenty of great services providing private tours in Chicago , but every tour on this list is one I’d happily take myself (if I haven’t already) and/or recommend to friends and family visiting the Windy City. So let’s jump in! 💃

My Top 3 Picks: Chicago Private Tours

Chicago Private Driver Tour

✅ Hotel Pickup

✅ Customizable Itinerary

✅ Knowledgeable Driver/Guide

45-Min Chicago Skyline Helicopter Tour

✅ See Chicago from above

✅ Noise Canceling headphones

✅ Free parking!

Lake Michigan Sailing Charter & Sightseeing

✅ Coast Guard certified captain

✅ BYOB & snacks

✅ Groups up to 6 welcome

Best 10 Chicago Private Tours

1. chicago private driver tour.

⭐️  RATING:  5/5 Stars | ⏳  TOUR LENGTH:  3-4 hours | ✅  Book Now!

Booking a guided tour of Chicago just for your group is the perfect way to have an exclusive luxury tour Chicago experience while making the most of your time in the Windy City!

First, you’ll be picked up directly from your hotel in a clean and comfortable Chicago private car, so you can start your sightseeing adventure right away. And there no need to book separate Chicago history tours!

Your guide will fill you in on all the history and stories of Chicago as you drive around, making stops at highlights like Lincoln Park Conservatory , Millennium Park, Museum Campus, and other notable attractions. See more of the city in a short amount of time without having to worry about navigating yourself or being stuck with long waits between locations. And if you want to see something that isn’t part of the tour, just tell your guide!

We had a foreign exchange student & decided to do the private tour in hopes that we might see a few different things & give her an idea of the city. It’s one of the best tours I’ve ever been on! jennifer w (read more Reviews )

🔑 Key Essentials

☑️ Professional local guide/driver ☑️ Private transportation ☑️ Pick up at your Downtown Hotel ☑️ Stroller/wheelchair accessible ☑️ All ages welcome ☑️ Infant seats available

🤩 Check Rates and Availability! 🤩

2. 45-Minute Chicago Skyline Helicopter Tour

⭐️  RATING:  5/5 Stars | ⏳  TOUR LENGTH:  45 Minutes | ✅  Book Now!

Soar high above the Windy City on a private 45-minute Chicago Skyline Helicopter Tour. Enjoy sweeping views of Chicago, including Navy Pier, Wrigley Field, Millennium Park , John Hancock Center, and Willis Tower.

This is the perfect way to celebrate any special occasion with someone special – this tour can accommodate up to three people comfortably!

Plus, you get the use of noise-canceling headsets so you can hear your pilot clearly as they take you on an unforgettable journey through the skies of Chicago. And you’ll get complimentary parking!

Whether you’re looking for a unique date night experience or just something to do with friends and family, this helicopter tour promises breathtaking views and an unforgettable adventure!

Flying over Wrigley Field – Where many family memories were made in the stadium and now over, Go Cubs! Katrina f (read more Reviews )

☑️ All Fees and Taxes included ☑️ Live commentary on board ☑️ Noise canceling headsets ☑️ Free Parking ☑️ Free photos of and in front of the helicopter! ☑️ Wheelchair/stroller accessible ☑️ Individual passengers must weigh less than 260 lbs

3. Lake Michigan Sailing Charter & Sightseeing Tour

⭐️  RATING:  5/5 Stars | ⏳  TOUR LENGTH:  2 hours | ✅  Book Now!

Experience the wind in your hair and the sun on your face as you explore Lake Michigan on a private sailboat. You and up to five other invited guests will have exclusive use of the boat, complete with captain and crew.

With BYOB allowed, bring along your favorite beverages (just no glass containers) to enjoy while taking in the sights of Chicago’s striking skyline. This is one of my favorite ways to spend an afternoon in Chicago!

Your captain can provide narration about different landmarks along the way, but if you’d like to customize the itinerary to suit your group’s interests, just let him know.

Plus, if anyone wants to take a turn at the helm, they can! Don’t forget a Bluetooth-enabled device so that you can play your tunes while out on the lake. There’s truly nothing quite like sailing away and feeling completely free! ⛵️

The sail boat was beautiful and very clean…We loved the views of the city from the lake. It was my favorite outing of our trip to Chicago. Our teen kids had a great time too. leslie m (read more Reviews )

☑️ Professional US Coast Guard licensed captain ☑️ Use of Bluetooth speakers ☑️ All applicable taxes ☑️ All ages welcome ☑️ Bring seasickness medicines if needed

👉 Get Dramamine for everyone! There’s even a chewable version available for kids.

4. History, Culture, and Architecture Walking Tour

⭐️  RATING:  4.8/5 Stars | ⏳  TOUR LENGTH:  2.5 hours | ✅  Book Now!

From iconic architecture to tasty treats, there are plenty of unique experiences that will make your visit to The Windy City unforgettable. This private guided tour can help you explore the Loop and get around like a local.

You’ll have the opportunity to see some of the greatest hits of Chicago, such as incredible old and new buildings, stunning river views, and much more. You’ll also enjoy some classic snacks like Chicago-style popcorn and homemade chocolate. You may also want to make time for visiting some of Chicago’s beautiful lakefront parks or museums so that you can feel the energy and buzz of this magnificent city. No matter your interests, booking a private tour is a great way for you to experience all that Chicago has to offer. With an experienced guide leading the way, you’re sure to have an experience full of memories that will last a lifetime.

It was one of the best tours I have been on. Dave…took us places I never knew existed in Chicago and he inspired us about Chicago and how very unique and fun the city is. nicole (read more Reviews )

☑️ English-speaking guide ☑️ Popcorn tasting ☑️ Chocolate tasting ☑️ Eco-certified, carbon-neutral tour operator ☑️ All ages welcome ☑️ Tour is available in groups or private, so be sure to choose the private option when booking!

5. Private Chicago Highlights Driving Tour

⭐️  RATING:   5/5 Stars | ⏳  TOUR LENGTH:  3 hours | ✅  Book Now!

Take this private tour of Chicago and discover the beauty and history of some of the city’s most iconic monuments.

Tour the vibrant neighborhoods like The Loop, River North, Magnificent Mile (Michigan Avenue), Streeterville, Gold Coast, and more with your own private driver-guide and vehicle. You can even go past the Chicago Art Institute!

Get up close to towering skyscrapers (some designed by Louis Sullivan!) in awe, explore beautiful architecture, and immerse yourself in the vibrancy of the city.

Plus with round-trip hotel transport included as well as bottled water, you don’t have to worry about transportation or hydration! Experience Chicago’s top sights with an expert local guide who provides you with personalized service.

The tour was wonderful and our driver, Juan, was terrific! Thanks for a great experience! jamie l (read more Reviews )

☑️ Downtown Chicago hotel/port pickup and drop-off ☑️ PrivateDriver/Guide ☑️ 3-12 participants ☑️ Stroller accessible ☑️ Infant seats available

6. Customized Private Walking Tour in Chicago

⭐️  RATING:   5/5 Stars | ⏳  TOUR LENGTH:  2 hours | ✅  Book Now!

One of my favorite ways to experience Chicago is through a customized private walking tour. With this best tour in Chicago by foot, you get to immerse yourself in the Windy City and its culture like never before!

With your knowledgeable guide, create an itinerary that meets all your individual interests, whether it’s history, architecture, street art, or Chicago’s food scene. And get recommendations for where to explore once the tour ends! Art, food, shopping, and architecture fans can enjoy Chicago sightseeing tours tailored just for them! But no matter which type of tour you choose, every tour is different and tailored just for private groups of up to 6 people. With a knowledgeable, private guide at hand, your day will be filled with amazing adventures that will give you memories that last a lifetime!

Dave was very friendly, knowledgeable and easy going. He took us to sites we had walked by many times without knowing the history. Our 18 year old was fascinated by the tour as well. kaaren a (read more Reviews )

☑️ CTPA Licensed Guide ☑️ Hotel pickup is available or meet at a location of your choice ☑️ Tours are available in English, French, and Dutch ☑️ Wheelchair and stroller accessible ☑️ All ages welcome

7. Private Walking Food Tour With Secret Foods

Your private walking food tour of Chicago is guaranteed to be the perfect way to explore the city’s most delicious eats! Delight in deep-dish pizza before your guide shows you sweet and savory treats that many visitors overlook.

As you go, you’ll get to learn about the history, architecture, and culture of this vibrant city. You’ll also enjoy enough treats and samples for a generous lunch along the way. Wander through downtown Chicago with an expert guide who knows all the hidden gems. Your private tour gives you access to some of Chicago’s greatest culinary secrets without any crowds or long lineups. For an unforgettable experience in one of America’s best cities for foodies, book this private walking foodie tour today! And be sure to show up hungry!

Sue…showed us great sites, pointing out interesting places that can be easily missed. Fabulous food! Every food stop was a winner. Enough food for lunch & supper. tripadvisor reviewer (read more Reviews )

☑️ Deep Dish Pizza with Sausage ☑️ Gourmet Popcorn ☑️ Chicago-style Hot Dog ☑️ Italian Beef Sandwich ☑️ Brownie ☑️ A delicious Secret Dish

8. All-Inclusive Chicago Foodie Tour: Windy City Favs

⭐️  RATING:   5/5 Stars | ⏳  TOUR LENGTH:  4 hours | ✅  Book Now!

Treat your taste buds to all the best Chicago has to offer with a private foodie tour of the city. This excursion Chicago offers all my local favorites, so you’re sure to enjoy it!

From deep-dish pizza and Italian beef sandwiches to hot dogs, and donuts, you’ll have a hard time deciding which tastes better. All while taking in some of the city’s most iconic sites like the Wrigley Building and Magnificent Mile.

Get an insider look at Millennium Park and The Rookery Building, among other landmarks. These local spots provide an authentic glimpse into the culture and history of this great city.

Your private guide will not only show you around the historic sites but also share stories and facts about each location that make it unique. Don’t miss your chance to explore Chicago’s top sightseeing spots while feasting on its famous eats !

Great hot dog!! A lot of insider info from the guide. Went to places I would have missed on my own! Learned a lot of history. Great communication leading up to the event. terri h (read more Reviews )

☑️ An Uber ride ☑️ English speaking tour guide ☑️ All tastes and fees ☑️ Bottled water ☑️ 1 Portillos hotdog ☑️ 1 small Garrett’s popcorn ☑️ 1 6-inch Al’s Italian Beef sandwich ☑️ 1 slice of deep-dish pizza ☑️ 1 Do-rite Donut ☑️ Stroller accessible ☑️ All ages welcome

9. Evening Sail in Chicago w/Navy Pier Fireworks

One of my favorite ways to spend an evening in Chicago is sailing while watching the Navy Pier Fireworks!

Treat yourself to an unforgettable experience on a private sailboat cruise that will take you along the beautiful lakefront of the iconic city. Enjoy a breathtaking view of the skyline as you watch the incredible fireworks from Navy Pier.

You and up to five others will have two hours to explore, customize your trip and make memories along the way.

Your U.S. Coast Guard licensed captain will be sure to provide a safe and intimate voyage, with your choice of music, route, and guest list so you can create a personalized evening worth remembering!

This was a great experience. Our captain was great and the view of the fireworks was breathtaking. Such an incredible experience. I defended recommend! freeman r (read more Reviews )

☑️ Professional US Coast Guard licensed captain ☑️ Use of Bluetooth speakers ☑️ All applicable taxes ☑️ All ages welcome ☑️ Bring Dramamine if anyone in your party is prone to seasickness

10. Chicago Lakefront Electric Bike Tour

⭐️  RATING:   5/5 Stars | ⏳  TOUR LENGTH:  1-2 hours | ✅  Book Now!

Make your Chicago experience one to remember with a private electric bike tour. Explore the city like never before, zipping along Lake Michigan and viewing the Chicago skyline from picture-perfect spots.

On your journey, you’ll see the iconic Buckingham Fountain, Field Museum, Adler Planetarium, and other landmarks.

Get up close and personal with the architecture, landmarks, and history of Chicago on this private electric bike tour. Your personal guide will provide an immersive experience as you ride along effortlessly on an e-bike.

Perfect for those 12+ who can ride their own full-size bike, this tour offers an unforgettable way to explore Chicago’s waterfront sights in record time.

Getting a close view of all attractions in Chicago, while having fun on a electric bike. Our tour guide was great and he even stopped to take photos! orece c (read more Reviews )

☑️ Use of bicycle and helmet ☑️ Bottled water & snacks provided ☑️ Participants 12+ only ☑️ Infant bike seats and tagalongs are not available

FAQs About Chicago Private Tours

Do you still have questions about private Chicago tours? Here are answers to some frequently asked questions.

How much is a tour guide in Chicago?

The cost of the tour depends on the size and type of tour you select. Group tours generally cost less than private tours, but they may not offer as much customization or personal attention.

Private tours are usually more expensive, but you will have a guide that is dedicated to providing you with a customized experience with personalized attention.

What is a private tour?

Creating a customized tour of any destination just for your group is a great way to ensure that you and your fellow travelers get the most out of your experience.

A private guided tour will allow you to tailor the itinerary to your exact needs, allowing more time for activities that interest your group and providing insider knowledge from our expert tour guides.

Are private tour guides worth it?

Yes, private tour guides are definitely worth it! Private tours provide a personalized experience that can’t be found in large group tours. With private tour guides, tourists have the chance to tailor the tour to their specific interests and needs.

Private tour guides also give tourists access to exclusive information and insights about the destination they are visiting that they wouldn’t get with traditional group tours.

What is the best way to tour Chicago?

The best way to tour Chicago is to book a private tour with a knowledgeable and experienced guide. This will ensure that you have the most comprehensive and enjoyable experience possible, as you’ll receive advice on the city’s top attractions tailored to your interests.

Furthermore, private tours allow for much more intimate and personal interactions than public group tours can provide. You’ll also be able to ask questions and get more in-depth information about the city’s history, culture, and architecture.

Why choose a private tour?

Private tours give you and your group exclusive access to the sights and attractions, allowing for a more personalized experience. Instead of having to stick to a generalized itinerary, your tour guide can tailor the tour based on your interests and preferences.

Depending on the size of your group, you may even be able to get time with the guide all to yourself! Private tours also come with additional benefits that are not available with regular group tours, such as priority booking for popular attractions like museums.

Should I get a tour guide?

Traveling can be an incredible experience for those who are looking to explore new places around the world.

But if you want to make sure that your trip is as enjoyable and memorable as possible, it’s important to consider how a tour guide can help you get the most out of your travels.

Are private tours safe?

A private tour with excellent reviews is definitely the way to go for extra peace of mind. Private tours will give you access to lesser-known spots, allowing for a more intimate and unique experience of the destination.

It’s also great for having some quality time with your family or friends without having to worry about large crowds or disturbances. Plus, reading reviews by previous customers can give an indication of the quality of the tour and help you pick the right one.

So yes, definitely choose a private tour with excellent reviews for that bonus peace of mind!

Is it better to travel with a tour guide or alone?

Traveling with a tour guide can definitely add value to your trip, depending on your goals. Tour guides can help you learn more about the culture and history of the places you visit, and provide valuable insights that you wouldn’t get otherwise.

On top of that, they often know the best places to eat, shop and find entertainment. They can also provide safety advice and show you around in areas where it might be difficult to navigate or communicate without knowing the language.

What is the difference between a group tour and a private tour?

Group tours are organized trips that involve traveling with a larger group of people. Typically, everyone on the tour follows the same itinerary and visits the same attractions. There’s no customization but the tradeoff is it’s generally cheaper.

Private tours allow for more personalization and freedom to tailor your experience. They may include private transportation, customized itineraries, and specialized guides. Private tours also tend to be more expensive than group tours due to their personalized nature.

🤩 The Chicago Private Driver Tour is the best choice for an exclusive, luxurious experience with maximum flexibility! 🤩

Final Thoughts: Private Guided Tours Chicago

Chicago private tours are the best way to make sure you see everything in the Windy City that you want to.

With so many unique districts and attractions, personal tours allow you to tailor your experience to what appeals most to you.

With an experienced guide, it’s easy to make sure you get a great view of every stop on your list. From stunning views of Lake Michigan to the endless nightlife of Wicker Park, there’s something for everyone in Chicago. No matter how much time you have in Chicago, there’s no better way to ensure you get the absolute most out of the city than with a private best Chicago tour.

So don’t wait any longer – check out one of these amazing options and book one of the private tours Chicago offers today!

Each of these experienced Chicago tour guides can show you all the sights that this incredible city has to offer and ensure that your experience is as amazing as possible.

🤩 Looking for other fun things to do in Chicago? While there aren’t any private options, the Chicago Architecture Tour River Cruise is one of my favorite group tours in Chicago! 🤩

👉 Awesome Festive Chicago Christmas Tours 👉 Top Spooky Ghost Tours in Chicago 👉 Fun Things to Do in Chicago at Christmas with Kids 👉 Unique Things to Do with Kids in Chicago at Halloween 👉 Kuma’s Corner Review: Best Burger in Chicago

Author: Brodi Cole

Brodi Cole is a full-time digital nomad who travels the world with her family. She made the switch to blogging and content writing after spending more than a decade and a half working as a Human Resources Manager and Director. Since transitioning her family to a digital nomad lifestyle, they've visited over 20 countries together (and counting) in the last ten years! In addition to traveling extensively through Canada, the USA, and the Caribbean, she's also visited Asia, Europe, and South America. She spent most of the pandemic living in Malaysia before living in Mexico for over a year and then driving the Pan-American Highway from the USA to the southernmost tip of Argentina. Brodi is also a freelance SEO writer and editor, sharing her expertise with other companies and bloggers. She has a Bachelor's Degree in English Literature and a Master's Degree in Human Resources Management.

Brodi Cole is a full-time digital nomad who travels the world with her family. She made the switch to blogging and content writing after spending more than a decade and a half working as a Human Resources Manager and Director.

Since transitioning her family to a digital nomad lifestyle, they've visited over 20 countries together (and counting) in the last ten years!

In addition to traveling extensively through Canada, the USA, and the Caribbean, she's also visited Asia, Europe, and South America.

She spent most of the pandemic living in Malaysia before living in Mexico for over a year and then driving the Pan-American Highway from the USA to the southernmost tip of Argentina.

Brodi is also a freelance SEO writer and editor, sharing her expertise with other companies and bloggers. She has a Bachelor's Degree in English Literature and a Master's Degree in Human Resources Management.

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BFDI & Inanimate Insanity 2024 Tour

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Show Run Time: 1 hour and 45 minutes Come experience a live premiere of two brand new BFDI & Inanimate Insanity episodes! The screening will be followed by a Q&A with the series creators! VIP ticket holders will also be able to meet the creators after the show. This event will be the event of the summer for the Object Show Community!

BFDI & Inanimate Insanity are two hit YouTube animated series created by Jacknjellify and AnimationEpic! The two creators have a combined following of over 2.5 million subscribers and nearly 2 billion views on their channels! For the first time ever this object show event is making its way to Chicago, where you can experience two brand new episodes live before anyone else!

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Enter for a chance to win a VIP trip to see Chicago & Earth, Wind and Fire!

Music legends Earth, Wind & Fire and Chicago , two of the most successful and critically-acclaimed bands of all time, are going back on the road for the return of their renowned co-headlining tour – Heart & Soul 2024 Tour . The 30-city tour kicks off on July 10, 2024 in St. Louis, MO and will hit cities all across North America before wrapping up in Palm Desert, CA on September 7, 2024. SiriusXM is giving YOU the chance to attend the Heart & Soul tour like a VIP!

One Grand Prize winner  will receive a round-trip airfare for two, including a 2-night hotel stay, and 2 VIP tickets to see Chicago & Earth, Wind and Fire!

VIP packages include:

Earth, Wind, and Fire – Let’s Groove VIP Package:

One premium reserved ticket to the show

One Earth, Wind & Fire lyric sheet

One specially designed Earth, Wind & Fire gift item, exclusive to package holders

One commemorative Earth, Wind & Fire VIP laminate

One commemorative Earth, Wind & Fire VIP ticket

Pre-show early tour merchandise shopping opportunity

VIP check in with early entry - VIP staff.

CHICAGO – 25 or 6 to 4 VIP Package –

One premium reserved ticket*

Chicago VIP merchandise with Chicago's Latest Tour Book

Exclusive Tour Poster of Chicago

Commemorative Chicago VIP laminate

Pre-Show early tour merchandise shopping opportunity

VIP check-in with early entry

On-Site VIP Ticket Host to check you in

Click here  for more information and tickets to see Chicago & Earth, Wind and Fire!

TELL US WHAT YOU LIKE AND GET MORE OF WHAT YOU WANT! After you enter, tell us your favorite SiriusXM shows and channels so we can tell you about more exclusive subscriber opportunities including invitations to private SiriusXM events, free tickets to concerts, movie screenings and sporting events, and much more!

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I spent $1,200 on tickets to see Olivia Rodrigo with my daughter. It was worth every penny.

• I wasn't able to get tickets for Olivia Rodrigo 's Guts World Tour at first.
• I didn't want my daughter to miss out on the show, so I bought resale tickets for $1,200.
• We had a great time together and seeing my daughter's joy made the cost worth it. 

When Olivia Rodrigo announced her Guts World Tour in support of her sophomore album, my body tensed.

"Here we go again," I thought. My daughter, 13, loves Rodrigo almost as much as she loves Taylor Swift.

Having tried, and failed, to get tickets through Ticketmaster for Swift's Eras Tour , I swore to do better.

Ultimately, I failed and ended up shelling out over $1,000 for two tickets to the tour. But I don't have any regrets.

I was determined to bring my daughter to the Guts World Tour

When Rodrigo announced the Guts World Tour , I did everything I could to prepare.

I recruited relatives to sign up their email for the Ticketmaster presale lottery so we'd have more chances to buy tickets. I even opened a credit card in hopes of getting access to the American Express presale.

When Rodrigo announced she was releasing $20 tickets in select cities, we once again rallied the troops to sign up for a chance to buy them.

We tried to get tickets to the show in our city, Washington, DC, and anywhere within reasonable driving distance, too.

We walked away defeated. Eventually, I realized Rodrigo would be performing in St. Paul, Minnesota, during our family trip there in March.

Related stories

But resale prices were high — two tickets with an unobstructed view were going to cost over $1,000. I put off making a decision.

The night of Rodrigo's first show, my daughter wondered aloud which songs would be on the setlist and what types of outfits the singer might wear.

My heart grew watching her excitement, and it quickly sank thinking she might miss out on seeing Rodrigio live. I worried ticket prices would climb even higher with the tour starting.

I panicked. Before Rodrigo's set ended, I'd purchased two tickets in the 110 section from resale marketplace TickPick for a whopping $1,200 after fees.

I felt incredibly fortunate that I could do this for my daughter, but still wondered if these tickets were a good use of money.

"It's a bad idea, right?" I told my daughter, quoting one of Rodrigo's songs. She assured me it was the best idea ever.

We had an amazing time, and I don't regret a thing

Once I had tickets, my daughter and I went all in, recapturing some of the magic we had preparing for Swift's Eras Tour .

My daughter carefully chose her outfit, working in several references to Rodrigo's songs, with ribbons in her hair and a homemade shirt. She even made me a matching one, even though we hadn't had matching outfits since she was a toddler.

She made me a friendship bracelet in Rodrigo's signature color, purple. I haven't taken it off yet.

When the concert started, my daughter was beside herself with joy.

As Rodrigo started her performance, my daughter's phone was fixed on the stage, but I was fixated on her. There's nothing better than watching one of my children experience happiness the way she did hearing Rodrigo sing live for the first time.

My daughter sang along to every single song. And, really, the show was incredible.

It was hard to look away as Rodrigo floated above the audience on a moon surrounded by stars. The 21-year-old singer acted like the rock star she is while also pausing to wave to fans.

I'm looking forward to going to more concerts with my daughter, but hopefully at more reasonable prices.

Watch: The Taylor Swift effect: How a pop star created her own economy

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To Sir with Love 's Lulu Says She Doesn't Speak Before Noon on Tour: 'I Take Care of My Instrument'

The "Shout" singer will embark on her farewell tour on Saturday, April 6

Kate Green/Getty

You make ( Lulu ) want to shout! But not before noon.

Speaking to the BBC earlier this week, the "Shout" singer revealed that she doesn't speak before noon when she's on tour to preserve her voice.

"I don't speak before 12 noon. I can understand why you think I'm lying," Lulu, 75, told the outlet. "But no. I'm very disciplined."

She adds, "I try not to come out of my room until 12. It makes it easier. I take care of my instrument. It allows me to sing."

On Saturday, April 6, Lulu — who rose to fame after the release of "Shout" at 15 — is embarking on her farewell Champagne with Lulu tour.

"To be honest with you, if when I was 15 years old and someone would have suggested I'd be doing a farewell tour when I'm 75, I'd have said, 'You are having a laugh,'" she said.

Adding, "You almost need an army to go on the road and I don't want to do it like this anymore."

Throughout the tour, Lulu will be joined by "special friends" and she'll perform the biggest hits from her discography.

Euan Cherry/Getty

Elsewhere in the interview, Lulu opened up about working with the late David Bowie on her version of "The Man Who Sold the World" in 1974.

"Bowie was a very special moment in my life," the "Oh Me Oh My" singer said.

"He made that single and we were going to do much more together. We had planned to do an album and I went to New York and did a couple of recordings," the To Sir with Love star added. "But David was on a certain trajectory in his life and he was over there and I was here doing my TV series and it didn't quite work out. Not that we didn't want it to."

Though Champagne with Lulu will be her final tour, the singer still plans to continue writing and recording music. And she still has one goal in mind for her music career.

"I want to sing a duet with Rod Stewart , I've never sung with Rod. That's on my wish list," Lulu said. "I think it's weird it's never happened."

"So, I've decided I may have to approach Rod at some point," she continued. "He may not answer my call though."

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