Chicago

15 Best Chicago Private Tours

This page gathers Chicago’s private tours and custom guides, priced per group rather than per seat. A family of four often comes out ahead of buying separate coach seats. Summer weekends go quickly, so reserve at least a week out.

1.Chicago Private Themed Escape Room Experiences

Immerse yourself in thrilling adventures! Try Chicago's private themed escape rooms and challenge your wits. Book now for an unforgettable experience in 2024!

Most Popular★ 5.0

“My wife and I visited The Escape Game Chicago last week and escaped our prison with just one second left ‼️ It was the perfect mix of thrill and challenge, and our game guide, Nathan, gave excellent clues that kept us on track without making…”

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2.Private Arrival Transfer From Chicago Airports (ORD) (MDW)

For a seamless and stress-free arrival in Chicago, the private transfer service from ORD and MDW airports offers door-to-door convenience and luxury transportation.

★ 3.5

“This was a painless experience. Communication was straight forward and easy. Our driver, Herze, was there within minutes of us stepping outside. The car was spacious and very comfortable. Herze was very personable and we had a great conversation. I would highly recommend this company.”

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3.Skip-the-Line Art Institute of Chicago Tour Semi-Private 8ppl Max

Marvel at the masterpieces of the Art Institute of Chicago with a skip-the-line tour, led by expert guides, and discover the stories behind iconic works of art.

★ 5.0

“Excellent overview of Museum highlights. Guide took us to the impressionists and the iconic paintings in the museum. He gave us a lot of background and history which was very interesting.”

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4.Private 45-Minute Chicago Skyline Helicopter Tour

Experience the breathtaking beauty of Chicago from a whole new perspective. Book your private 45-minute helicopter tour and soar above the iconic skyline today!

★ 5.0

“Everything! The experience of this helicopter ride in general will always be memorable. Being able to see the changing of the leaves from above. Matt's knowledge of Chicago, his kindness & patience was truly appreciated.”

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5.Best of Chicago: Architecture & Highlights City Private Tour

Knowledgeable guides lead visitors on a captivating 3-hour walking tour, unveiling the architectural wonders and cultural highlights that make Chicago a must-visit destination.

★ 5.0

“Great walking tour, learnt many facts & tasted some local treats. Rich was a great guide, we were even treated to his rendition of a couple of songs & some music to walk the Pedway!!! Highly recommend”

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6.Private Departure Transfer to Chicago Airports (ORD)(MDW)

Get to Chicago airports in style and comfort with our private departure transfer service. Skip the hassle and book your ride now.

“Driver was early. He was very patient and helpful. He was very, very friendly. He helped with the luggage without asking. He was open to my suggestion for the quickest route to the airport.”

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7.Art Institute of Chicago Private Expert Guided Tour

Keen to explore the Art Institute of Chicago's extensive collection with a private expert? This guided tour offers a captivating and personalized experience.

★ 5.0

“Our tour was a semi private one. It ended up being private because no one joined except us. Our tour guide was Brian Gallagher and he was an excellent guide. His knowledge of the art, the history of it, and how it came to Chicago…”

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8.Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

Discover the beauty of Lake Michigan and Chicago's stunning skyline on a private sailing charter. Experience the ultimate adventure with breathtaking views. Book your tour now!

★ 5.0

“A great time out on the lake. Our captain was very capable and informative. I would recommend for just a fun experience or for a special occasion.”

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9.Private Chicago Fire TV Show Set Tour

Captivating fans with an exclusive behind-the-scenes look at the hit TV series

“Deen is an amazing tour guide and he has so much education and was so knowledgeable with all places that he shared with us on the tour! This tour went beyond our expectations and I would highly recommend it!”

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13.OHare Airport (Curbside) To Chicago, Luxury Private Sedan, All Inclusive

Experience luxury and convenience with our all-inclusive private sedan service from O'Hare Airport to Chicago. Skip the hassle and enjoy a stress-free ride. Book now!

★ 5.0

“Driver wasn't waiting but no biggie beause after a quick call they arrived within 10 mins. However the driver was non communicative and made the ride a little weird and didn't offer water which we've revived with other companies. I appreciate this is a city…”

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14.Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Discover the hidden gems of Chicago on a personalized 2-hour walking tour. Explore the city your way and make unforgettable memories. Book your private tour now!

“Leentje was so friendly, knowledgeable and provided us with such a wonderful tour. I would definitely recommend her to others.”

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15.Chicago: Private Helicopter Tour of Chicago Skyline

Experience the breathtaking beauty of the Chicago skyline like never before with a private helicopter tour. Fly high and capture stunning views. Book your adventure now!

★ 4.4

“We had a really good time. I loved our pilot. He looked just like Patrick Swayze and he was very, very sweet and informative. Would definitely do this again.”

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4.4Chicago: Private Custom Tour With a Local Guide2 - 8 hours$129 5.0Private Sunset Sail on Lake Michigan With Breathtaking Views of Chicago2 hours (approx.)$507.96 5.0One-Way Private OHare Airport Curbside Transfer by SUV30 minutes to 1 hour (approx.)$160.00 5.0Private Chicago Scenic Driving Tour2 hours (approx.)$315.00 5.0Midway Airport (Curbside) To Chicago, Luxury Private Sedan, All Inclusive30 minutes to 1 hour (approx.)$133.00 5.0Downtown Chicago To OHare Airport – Luxury Private SUV, All Inclusive30 minutes to 1 hour (approx.)$155.00 4.5Round Trip Private Transfer ORD Airport to Chicago City Oak Brook20 to 40 minutes (approx.)$91.66 5.0Meet and Greet Private SUV Transfer From ORD to Downtown Chicago$300.00 5.0One-Way Private Transfer From Downtown Chicago to ORD by Sedan30 minutes to 1 hour (approx.)$133.00 4.5One-Way Private OHare Airport Meet and Greet Transfer by SUV30 minutes to 1 hour (approx.)$200.00 4.8Chicago: Private 3-Hour Al Capone Gangster Tour3 hours$880 5.0Private Sedan Transfer From Chicago Downtown to OHare Airport30 minutes to 1 hour 30 minutes (approx.)$220.00 3.0Chicago Private One-Way or Round-Trip Luxury Airport Transfer (Feb )30 minutes (approx.)$228.94 5.0Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour3 hours$950 3.5Private Frank Lloyd Wright Architectural Tour by Luxury Vehicle – 3 Hours$300.00 4.5Private Al Capone Gangster Tour in Chicago$539 4.0Chicago: Private Architecture Tour – 3 or 6 Hours$780 5.0OHare Airport (Greet & Meet) To Chicago, Luxury Private Sedan, All Inclusive30 minutes to 1 hour (approx.)$154.00 4.5Private Frida & Friends Tour in Pilsen2 hours (approx.)$240.00 4.0Chicago Private Smartphone Scavenger Hunt Game and Tour2 hours (approx.)$7.20 5.0Chicago Architecture Walking Tour (Private & All-Inclusive)3 hours (approx.)$211.00 4.8ORD Airport Private Transfer To/From Chicago$85 5.0Chicago Private Foodie Tour: Windy City Faves4 hours (approx.)$288.00 5.0Private Chicago Tour With Driver and Tour Guide. Hotel Pick up Included4 hours (approx.)$844.59