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Top picks for Chicago Experiences

Q: How many Experiences are available in Chicago on Trip.com?

Trip.com offers 9 Experiences in Chicago

Q: What are the best Experiences in Chicago?

Chicago CityPASS Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more) BIG BUS Chicago hop-on hop-off bus tour

Q: What are the top-rated Experiences in Chicago?

BIG BUS Chicago hop-on hop-off bus tour Chicago CityPASS Chicago: Ultimate City Attractions Bike Tour

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Q: Can I change or cancel my booking?

Change and cancellation policies vary by attractions and tours. Please check the product details page for more information.

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Ticket prices may vary between weekdays and weekends, as well as during peak and off-peak seasons. When booking with Trip.com, you can also use Trip Coins to get extra savings. For more tips on booking discounted tickets, please visit Trip.com for the latest information.

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Discover 9 Experiences in Chicago on Trip.com, updated January 18, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From HKD 60.79 per person, with an average total of HKD 497.83. Choose the option that suits your plan.

With 1.795k verified reviews, Experiences Chicago boast an average rating of 4.7.

This week's most popular Experiences: "Chicago Crime and Mob Bus Tour ", with 1.593k reviews and a 4.7 rating.

Now on Trip.com: "Chicago: Mob and Crime Bus Tour", a 1-hour adventure in Chicago!

The next available day tour departs on January 19, 2026. Book now to secure your spot!

Chicago Experiences usually take about 1 hours — perfect for a relaxed, immersive experience!

100% of Chicago Experiences now offer English-speaking guides

January is perfect for visiting Chicago! Choose from Experiences available day tours, including seasonal hits like Chicago Crime and Mob Bus Tour .

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

Search attractions or local attractions & tours

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9 results for Chicago Experiences

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Recommended

Chicago CityPASS
English
4.9/5
Excellent· 25 reviews· 261 booked
FromHK$1,091.74
Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more)
English
4.0/5
Good· 2 reviews· 77 booked
FromHK$655.05
BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Excellent· 3 reviews· 61 booked
FromHK$282.13
Flyover in Chicago: An Immersive Flying Theatre Experience
Duration: 30 mins
English
4.8/5
Very good· 99 reviews
FromHK$296.17
Chicago Crime and Mob Bus Tour
Duration: 90–120 mins
English
4.7/5
Very good· 1.6k reviews
FromHK$382.11
Chicago: Mob and Crime Bus Tour
Duration: 1.5 hrs
English
4.7/5
Very good· 53 reviews
5% off
Limited-time sale
FromHK$362.63HK$381.72
Chicago City Day Tour
Duration: 5.7 hrs
English
4.5/5
Satisfied· 4 reviews
FromHK$1,169.73
Chicago CityPASS: 5 attraction admission tickets
English
FromHK$1,126.79
Go City Chicago Explorer Pass - Go City Chicago Explorer Pass
English
FromHK$654.77
Chicago: Ultimate City Attractions Bike Tour
Duration: 3 hrs
English
4.9/5
Excellent· 9 reviews
5% off
Limited-time sale
FromHK$436.60HK$459.58
Book after inquiry/Route 66 Willis Tower Robie House Lincoln Park Airport in Chicago, USA/Point-to-point car service/Tour guide and driver/Private car service
English
FromHK$741.57
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
English
FromHK$60.79
Studio W.I.P. - Uptown Chicago: Spray Paint & Sip Urban Art Workshop
Duration: 90 mins
English
FromHK$349.80
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
English
FromHK$60.79
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromHK$233.87
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
English
FromHK$60.79

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Frequently asked questions about Chicago Experiences

How many Experiences are available in Chicago on Trip.com?

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What are the best Experiences in Chicago?

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What are the top-rated Experiences in Chicago?

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Can I change or cancel my booking?

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How can I get discounted prices?

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Trip.com Picks

Popular Chicago Tours

Best Chicago Experiences

Popular Activities

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Reviews/Trip Moments

★

Reviews: Chicago CityPASS

Guest User2026-01-03

This citypass is good idea for tourist easy to manage. We can visit Chicago in a short time with good memories. I will recommend to my relatives and friends if they visit Chicago.

★

Reviews: Go City: Chicago Explorer Pass (Discover over 30 top attractions | 360 CHICAGO, Skydeck Chicago & more)

Guest User2024-12-07

Easy to use and good choice and savings for short trips

★

Reviews: BIG BUS Chicago hop-on hop-off bus tour

Guest User2025-11-06

It’s a nice experience for those who have a short visit to Chicago. One can see the main attractions and city highlights in 24 hrs ticket. 48 hrs ticket only recommended if wishing to use the cruise, otherwise 24 hrs are enough to see the city

★

Reviews: Flyover in Chicago: An Immersive Flying Theatre Experience

Guest User2025-12-21

It was very cool and exciting. I would add more Chicago themed attractions. MJ (Micheal Jordan) is a huge staple in Chicago and he nor the entire South Side was featured. The actual journey was a lot shorter than I expected.

★

Reviews: Chicago Crime and Mob Bus Tour

Guest User2025-12-06

Great tour. Very knowledgeable guide. Highly recommend. I really enjoyed learning so much about the crime history of Chicago.

★

Reviews: Chicago: Mob and Crime Bus Tour

Guest User2026-01-10

Lots of information given and the guide made it interesting. The speed of the conversation made it sometimes hard to listen

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