private tours in chicago

Luxury Private Tours | Bespoke Experiences

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chicago private tours

BESPOKE HISTORY

international influence

BESPOKE ARCHITECTURE

eclectic designs

BESPOKE LIFESTYLE

authentic culture

BESPOKE DINING

delectable cuisine

BESPOKE LANDSCAPES

natural scenery

BESPOKE EXCURSIONS

unforgettable adventure

Experience Chicago  

Our city your way ™, reimaging the luxury chicago private tour experience: uncompromised luxury.

Personalized itineraries. Flexible schedules. Private small groups.

More than a private tour, your luxury travel experience doesn't exist until we custom design an itinerary unique to your needs.

Chicago ~ also known as The Windy City, Chi-Town, Second City, The 312 ~ will knock your Sox off once you grant our gracious local guides an opportunity to showcase its glamorous and gritty history, with everything in between during your private customized experience. Bypass the crowds with a private architectural tour of city landmarks, peruse the upscale boutiques of the Magnificent Mile and access the diverse neighborhoods with an insider during your city overview. Our time is your time, and we’ll design your days as you wish.

Any time of the year, Chicago has something to offer visitors, both indoor and outdoor. Whether you seek high class or low-brow, skyscrapers or underground, snowy winters or sunny summers, we’ll utilize our resources, network and skills to engage and entice your private small group during your custom luxury tour.

Truly Bespoke Designs Range From:  $ 2 ,000 - $200,000 and beyond  

(Chicago private tours include: custom design, project management, transportation, ambassador & gratuity)

    How it Works

Influential History

Chicago grew from a small river-based trading post into a booming multicultural center of commerce and creativity. Although the Great Fire of 1871 devastated much of the young city, it rose from the ashes to become a modern center of opportunity – a reputation it proudly maintains today balancing tradition and innovation, welcoming people and businesses from around the world. Incorporate history into your Chicago Private Tour.

Eclectic Architecture

While much of the city’s original architecture was lost, Chicago moved forward, shaping its own destiny in the form of prominent architecture from Art Deco to Post-Modern. Known as the birthplace of the skyscraper, Sullivan’s structural innovation created an avenue of opportunity for prolific builders influencing diverse Chicago neighborhoods from north to south, including the first 20 years of Frank Lloyd Wright’s impressive career. Incorporate architecture into your Chicago Private Tour.

Authentic Lifestyle

With 26 miles of lakefront, 552 parks, beaches, bike trails, and ever-busy streets, Chicagoans enjoy four distinct seasons of entertainment and activity. Five major-league sports teams, the renowned Art Institute of Chicago, theaters, an acclaimed symphony center, ethnically diverse cultural centers, and chic shopping along the Magnificent Mile ensure Chicago’s 40 million annual visitors leave with memories that will last. Incorporate lifestyle into your Chicago Private Tour.

Delectable Dining

Whether you choose ninety-five stories above, or several feet under-ground, water-front, curb-side or Michelin-starred, Chicago is home to much more than just deep dish pizza and famous hot dogs. The city’s drinking culture, infamous since Prohibition lets you sneak into a speakeasy from a bygone era for a relaxing cocktail, or indulge your taste for the best of the Midwest’s established microbrewery culture. Incorporate dining into your Chicago Private Tour.

Natural Landscapes

Lake Michigan and the Chicago River provide an aqueous backdrop to the manmade structures of Chicago’s picturesque skyline, granting guests an opportunity to explore the Windy City at sunset with a Chicago River cruise from Navy Pier. If you prefer a grounded approach, we’ll bring the family to the vast Botanic Gardens or escape winter’s chill amidst the lush temperate foliage of The Garfield Park Conservatory. Incorporate landscapes into your Chicago Private Tour.

Unforgettable Excursions

As the largest city in Illinois, Chicago has no shortage of adventures awaiting you within, and beyond, the city limits. Explore one of the Great Lakes by boat, head to Grosse Point Lighthouse, or we’ll explore the various state parks. Further afield, enjoy an expedition along the lakeshore sand dunes with bird sanctuaries. And did you realize the states of Indiana, Wisconsin and Michigan are each less than two hours away? Incorporate excursions into your Chicago Private Tour.

THE GREATEST LUXURY TODAY IS SERVICE: Our Philosophy

We're not alone in believing Chicago is one of the most extraordinary cities in the world. We believe you deserve an opportunity to enjoy more of our beloved home, delving deeper than the surface. Let us invest time to choreograph your own rich, meaningful adventure.

By definition, we believe your experience should be as unique as you.

Bespoke is your definitive source for a private, fully escorted luxury travel experience in Chicago.BESPOKE IS YOUR DEFINITIVE SOURCE FOR A CHICAGO PRIVATE TOUR, A FULLY ESCORTED LUXURY TRAVEL EXPERIENCE.

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We’ll handcraft your sophisticated travel experience expertly tailored to your individual needs.

To begin the design process, please call or email us today. Click  HERE for our Contact Us page.

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(312) 265-4645

Chicago Private Tour Experiences

Classic city tour, frank lloyd wright.

This 3-4 hour tour includes driver, guide and vehicle and is designed to cover history and architecture by visiting all major sites, including favorites such as the Magnificent Mile, Gold Coast neighborhood, Wrigley Field, Navy Pier, Millennium Park, Museum Campus, Obama's home, the public art and skyscrapers of the Loop and more.  Each tour has built in photo/walking stops, but should you desire something specific, that can be built into your itinerary.

This 2 hour tour includes driver, guide and vehicle and is designed to cover history and architecture by visiting the city center and choosing to visit  either the north side (Wrigley Field) or the south side (Hyde Park, University of Chicago Campus, Museum of Science and Industry, Kenwood Mansion District).

​Each tour has built in photo/walking stops, but should you desire something specific, that can be built into your itinerary.

chicago craft beer tour

This 3-4 hour tour includes transportation and tickets to Oak Park, IL to visit both FLW's Home & Studio and ~20 other homes he designed in the surrounding neighborhood.  ​Because of the popularity of this location, tickets are often in limited supply. Also, the combination of sites and group, self-guided and private tours makes it necessary to call or email for pricing and availability.

This 3-4 hour tour visits several local breweries. Each brewery offers a variety of tastes as unique and diverse as Chicago! Sample some of the many rich micro-brews of Chicago, made from seasonal hops and malts, as well as a possible peek into the brewing process. Learn about the rich stories of Chicago’s brewing history, how alcohol fueled famous gangster rivalries, and other fun Chicago history. This tour itinerary is completely customized based on date, start time and budget.​ (Must be 21 years old or older. Please bring ID as breweries require them for entry.) 

Jazz and blues Tour

This 3-4 hour tour provides transportation and guide!  You will visit  2-3 live music venues, as well as a few stops for ideal City Lights gazing. This tour itinerary is completely customized based on the desired tour departure date, start time and budget.

​(Must be 21 years old or older. Please bring ID as music venues require them for entry.)

Holiday Tour

Enjoy the breathtaking views of architectural masterpieces, from Probst & White to van der Rohe, terra cotta clad French Renaissance details to minimalistic industrial steel framework and large glass panes. Your guide will show you what makes this city so spectacular, and with a holiday flare! Holiday stops include Daley Plaza's Christkindl Market, Macy's Walnut Room and animated story windows, the Goodman Theatre, and marvel at the skaters under the iconic "Bean" of Millennium Park. 

NOVEMBER/DECEMBER

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Chicago Guided Tours-

Explore chicago's wonders with exclusive guided tours by babylon, chicago city tours.

• Museum Tours
• Walking Tours
• Combo Tours

Field Museum of Natural History Chicago - Skip-the-Line Guided Tour

2 - 2.5 Max

125 years in the making, this collection now exceeds 40 million artifacts. On this 2.5 hour guided museum tour, your guide will navigate the labyrinth to ensure you see the best of the best: from Sue the T-Rex, to the hall of Jades, and the largest mummy collection in North America.

Semi - Private

Private Tour

The Art Institute of Chicago - Skip-the-Line Guided Tour

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way.

Art of a City, Downtown Chicago Guided Walking Tour

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. This 2.5 hour guided walking tour is perfect for busy sidewalks and getting up close to monumental art!

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10 Best Chicago Private Tours to Book in 2024

Sharing is caring!

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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Private Tours in Chicago

Multilingual experiences with friendly, professional service, local, multilingual guides, private, customizable tours, group options available, let us show you chicago, a private vehicle tour tailored to you.

We are proud to offer all of our tours in English, Spanish, and Portuguese so that you feel at home in our beloved Chicago. What’s more, all of our tours are private and in our own vehicles ; you’ll get around Chicago quicker and see everything that you came to see, in comfort and style . Just let us know what’s on your list and we can accommodate! We have a 3-hour , 4-hour , and even full-day tour , so however long you need is completely up to you .

Private Chicago Highlights Driving Tour

Private chicago extended highlights driving tour, private complete chicago driving tour, frank lloyd wright home & studio experience, layover tour, add on tickets to your chicago adventure.

Chicago has so many incredible things to do and see , it can be hard to know where to start! To help you, we have hand-selected a fantastic range of popular attraction tickets , so you’ll get to see the best city attractions in an easy, reliable way! From cruises on Lake Michigan to a luxury Skydeck breakfast , we promise a great variety of activities to enrich your Chicago experience.

Chicago CityPASS

Chicago helicopter ride, spirit cruise on lake michigan, odyssey cruise on lake michigan, chicago architecture boat tour, chicago extreme speedboat ride, skydeck cafe, odyssey cruise on the chicago river, 360 chicago observatory and tilt experience, bring your group to chicago, we offer specialized group itineraries.

If you are in Chicago or looking for a destination for a group trip, look no further! Our unique array of contacts throughout the city of Chicago allows us to organize exclusive itineraries for any type of group , whether it be for work or pleasure . To learn more about what we can offer your group, please click the corresponding button. If you are interested in what we have done in the past, feel free to sign up using the button below , and we’ll email you a PDF with itineraries we’ve done before !

Customized MICE Tours

Custom leisure tours, need to get somewhere, speak another language, check out our site in spanish or portuguese, we proudly partner with the following, have more questions, please get in touch with us.

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Chicago Private Tours and Productions

Custom Chicago Private Tours | VIP Experiences – Special Events

Private Tours & Pricing

Customize your chicago experience  .

Why settle for a generic, public Chicago touring experience when you can curate a customized, private tour exactly to your likes and interest? That’s the guarantee we provide you here at Chicago Private Tours and Productions.

Check out our most popular private tours of Chicago below:

Chicago Architecture Tour :

Despite the Great Fire that once ravaged the city of Chicago over a century ago, the city is credited as the birthplace of the modern skyscraper. Chicago is so renowned for architecture that it’s the most vertical metropolis from here to Hong Kong.

On our Chicago Architecture Tour, we’ll stop at and discuss:

• Sears “Willis” Tower
• The John Hancock Building
• Gothic gems
• Magnificent Mile notable locations
• Historic brownstones
• The Frank Lloyd Wright homes of Oak Park

We offer a uniquely added value opportunity to view not only the outside, but also explore the inside of many of these infamous buildings. Our tour will satisfy the architecture style and structural tastes of the most discerning traveling.

CLICK HERE TO BOOK NOW

Chicago food tour :.

Savor Chicago’s signature dishes at local, hidden eateries, showcasing the city’s love affair with foodie indulgence.

On this tour, prepare your taste buds for:

• Chicago Dogs in Wrigleyville
• Deep-dish pizza in Little Italy
• China Town exploration
• Ukrainian Village introduction
• Greek Town introduction

Quite simply: this tour is a movable feast!

The Chicago Speakeasy Pub Crawl:

Our Prohibition Era Speakeasy Pub Crawl is filled with cocktails and a perfect venue for bachelor or bachelorette parties, corporate events, or just a fun night out on the town to celebrate life and your friends. Hosted by a local historian, dressed in period clothing, the tour makes stops at:

• Al Capone’s neighborhood
• Old Chicago bars
• Prohibition era establishments  

We transport you back in time to the 1920s, entering our venues through secret openings that really shed light on what the city was like 100-years ago. Relive the glamour of this time period while listening to stories of the rampant racketeering and bootlegging. If you’re really feeling up to it, dress the part, too.

Custom Chicago City Tour:

We’re ready to put the “custom” in Custom Chicago City Tours. What venues are you dying to see? What history are you dying to learn? Are you ready to personalize your excursion, custom tailored to your unique likes and interests?  

We’re ready to answer the challenge. We want to provide a private Chicago tour your will never forget. Identify whatever captures your attention and imagination, whether it’s food, architecture, history, drinks, and the list goes on.

We’ll plan your tour and make it happen.

Chicago’s Neighborhoods Tour:

The city of Chicago is known not only for its iconic skyline, but also its distinctive historic neighborhoods – and the locals that give them their vibrancy. The neighborhood vibe changes from block to block, with our educated tour guides ready to shed light on the history and culture that comprise each microcosm.  

During our Chicago community tour, visit stately homes and massive structures of the white city, built on the site of the World’s Fair in President Barack Obama’s neighborhood of Hyde Park. Smile with locals who live across the street from Wrigley Field, waiting to catch a home run hit baseball.

This is a tour that delivers an appreciation of old world culture, saturated with Chicago’s different and unique districts.

Magnificent Mile Shopping Tour:

For the shoppers of the world, did you know Chicago is a shopping paradise? Hit some of the most famous shopping enterprises in the country with a personal Chicago fashion designer as your tour guide.  

Crammed with exciting perks, our Michigan Ave. Shopping Tour patrons can enjoy special access to designer showrooms, rare opportunities to meet with the fashionistas that influence Chicago’s fashion scene, and exclusive discounts on special purchases. Plus, you’ll receive introductions to the hottest new store brands and shops along Michigan Avenue, as you make your way down the Magnificent Mile.

To all the shopaholics, avid browsers, and curious tourists with a taste for consumerism, you’re going to love this Chicago fashion and shopping tour.

Chicago Gangster Tour:

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons.  

Visit the old stomping grounds of:

• John Dillinger
• The Untouchables

View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the St. Valentine’s Day Massacre.

We bring Chicago’s true crime past to life before your very eyes.

Chicago Haunted History Tour:

Up for more of a spooky perspective of the Windy City? Boy, does it deliver. We have curated a unique and underground ghost tour, providing you with the rare opportunity to visit many of Chicago’s notable haunted locations.  

Some of the infamous tour stops include:

• Murder Castle : the hotel designed specifically for murdering people in the late 1800s by America’s first mass serial killer: H.H. Holmes.
• Death Alley : Peruse a haunting pathway where hundreds of theater patrons were stacked after perishing in the great fire at the Iroquois Theater
• Old Congress Hotel : Once the full time residence of its former owner, Al Capone, there are ghosts and spirits that haunt the hallways of this famed location.

Different from other tours, our Haunted Chicago Tour is guided by a historian, providing insight into the historical events, information, persons, and rumors of the past. Our guides provide historically documented tales of hauntings told in a “camp fire” style fashion. It’s as intimate and haunting as you can possibly experience Chicago.

PER TOUR PRICING (3-HOUR TOURS):

• MERCEDES S 550 AMG (1-2 PASSENGERS): $660
• CADILLAC ESCALADE (3-5 PASSENGERS): $780
• MERCEDES SPRINTER (6-12 PASSENGERS): $900
• LUXURY MINI COACH BUS (13-24 PASSENGERS): $1440
• LUXURY COACH BUS (25-39 PASSENGERS): $1740
• LUXURY MOTOR COACH BUS (40-55 PASSENGERS):$2140

For those wishing to book a tour of more than 55 people, we are happy to accommodate you! We ask that you call or email us, and we can begin planning out the details for your private tour of Chicago.

CONTACT US TODAY

Phone: 1-708-239-8602

Email: [email protected]

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CURATED EXPERIENCES

For curious people.

We are a boutique experiential company that connects people to each other and their physical environments through storytelling and creative activities.

Corporations, universities, and museums consult with us for community building activities that incorporate chicago stories:  , – visitor experience strategy, – corporate field immersions , – experiential learning programs, – custom in-person tours, – virtual experiences for remote teams.

virtual TOURS for COMMUNITY building

With our  virtual tours , guests see stunning visuals and hear stories across time of  women’s history, the 1893 World’s Fair, Chicago food and drink, the Chicago River and more. As featured in  Entrepreneur Magazine . 

Live facilitators recount the big ideas and personalities across Chicago history.

Guests virtually travel through time and space via historic illustrations, 360-degree photos, and other beautiful visuals.

CONNECT REMOTELY

Creative challenges, competitive games and reflection exercises promote collaboration and connection.

custom tours and content

We work with corporations, non-profits, and marketing agencies to design and produce hyperlocal stories via visual, written and experiential media. 

Our corporate Clients

Chicago Detours is passionate about connecting people to places and each other through carefully designed and curated experiences. 

Originally a tour company, we built a reputation for having not just some of the best tour guides, but also having incredible storytellers and experiential designers. 

Chicago Detours is a team of educators, historians, journalists, and creators. We are passionate about the power of storytelling. 

Originally a tour company, we also produce hyperlocal digital content like virtual tours and documentary videos. 

ready to brainstorm with us?

Book a tour, latest from the blog.

Tour Guides are Storytellers

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Let’s Connect!

Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.

Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

Amanda Scotese

Executive director and tour guide.

Road Trip Chicago - Private Tours

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Please text or email all tour requests to: 630-702-9364 or [email protected]

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Private tours in Chicago

Time of day.

• Architecture
• City Highlights
• Family Friendly
• First Time Visitor
• Off the beaten path

Attractions

• Chicago-style deep dish pizza
• George Pullman
• Hancock Tower Observation Deck
• Hotel Florence
• Millennium Park
• Pullman Clock Tower
• Pullman District
• The Magnificent Mile

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