Top picks for Chicago Experiences

Discover 38 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 MXN 137.35 per person, with an average total of MXN 1,152.83. Choose the option that suits your plan.

With 1.84k 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 Full Day Bike Rental", a 24-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 24 hours — perfect for a relaxed, immersive experience!

86% 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.

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38 results for Chicago Experiences

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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: Chicago Full Day Bike Rental
Guest User2025-10-18
Easy process, great communication, rode the 7 speed city comfort bikes to Evanston and back. A very enjoyable ride. Appreciated the locks included in the rental.
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