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.
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…”
★★★★★★★★★★
332 reviews1 hour 15 minutes (approx.)From $47.95by The Escape Game Chicago
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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.”
★★★★★★★★★★
196 reviews1 hour (approx.)From $89.60by Carmel Car & Limousine Service
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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.”
★★★★★★★★★★
157 reviews2 hours 30 minutes (approx.)From $85.50by Babylon Tours Chicago
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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.”
★★★★★★★★★★
126 reviews45 minutes (approx.)From $849.00by Heli Chicago
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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”
★★★★★★★★★★
94 reviewsFrom $245.00by WeVenture
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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.”
★★★★★★★★★★
91 reviews1 hour (approx.)From $89.60by Carmel Car & Limousine Service
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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…”
★★★★★★★★★★
84 reviews2 hours (approx.)From $215.00by Chicago Museum Tours
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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.”
★★★★★★★★★★
70 reviews2 hours (approx.)From $566.82by Come Sailing, Inc.
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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!”
★★★★★★★★★★
68 reviews2 hours (approx.)From $315.00by Deen Ajeigbe
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Discover the hidden culinary gems of Chicago on a private walking food tour. Uncover secret food spots and indulge in a mouthwatering adventure.
“Need to walk and be hungry. This was an awesome combination of history of Chicago food but all history.”
★★★★★★★★★★
61 reviews3 hours (approx.)From $224.99by Secret Food Tours
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Skip the hassles of public transportation and enjoy a smooth, private arrival transfer from Chicago airports ORD or MDW. Start your trip stress-free!
★ 3.5“She was on time, friendly, and knowledgeable It was very appreciated to be able to text and be able to talk to her as needed”
★★★★★★★★★★
54 reviews30 minutes to 1 hour (approx.)From $50.00
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Yearning for a seamless arrival in Chicago? Discover how a private transfer from O'Hare Airport can elevate your travel experience and make your journey stress-free.
★ 4.2“Thank you for great service! The drive to my hotel was smooth! A great start for my first time in Chicago!”
★★★★★★★★★★
46 reviewsFrom $40by Elife Ride
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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…”
★★★★★★★★★★
41 reviews30 minutes to 1 hour (approx.)From $133.00by Echo Limousine
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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.”
★★★★★★★★★★
35 reviewsFrom $220.00by Chica-GO Off The Beaten Path Tours
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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.”
★★★★★★★★★★
29 reviewsFrom $188by Paratus Air (FlyHeli)
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