Top picks for Chicago Experiences

Discover 38 Experiences in Chicago on Trip.com, updated January 13, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From MXN 139.47 per person, with an average total of MXN 1,184.62. Choose the option that suits your plan.

With 4.411k verified reviews, Experiences Chicago boast an average rating of 4.7.

This week's most popular Experiences: "Chicago Crime and Mob Bus Tour ", with 1.59k 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 14, 2026. Book now to secure your spot!

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

88% 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: Chicago: Mob and Crime Bus Tour
Guest User2025-11-30
I really enjoyed the content, however, the guide spoke very fast. She was friendly, but for foreigners, she could have been slower… I think they could add a stop with some kind of drink or food during the tour…
Contact Center <br>of the year 2025
Contact Center
of the year 2025
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