Top picks for Chicago City passes

Discover 142 City passes in Chicago on Trip.com, updated November 2, 2026, with experiences lasting from 1 to 8 hours. Find the perfect adventure for your day!

From TWD 267 per person, with an average total of TWD 2,226. Choose the option that suits your plan.

With 7.257k verified reviews, City passes Chicago boast an average rating of 4.8.

This week's most popular City passes: "Chicago Architecture River Cruise", with 4.695k reviews and a 4.9 rating.

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

The next available day tour departs on November 3, 2026. Book now to secure your spot!

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

47% of Chicago City passes now offer English-speaking guides

November is the perfect time to visit Chicago! Choose from 142 available day tours, including seasonal favorites like Chicago Architecture River Cruise.

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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142 results for Chicago City passes

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Trip.comChicago
City passes

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See what other travellers love, based on ratings and bookings

RecommendedAttractions (47331)Boat tours (41)Shows & events (2)Culture & history (58)Day tours (145)Food & drink (27)Outdoor & sports (2)City sightseeing (60)Nature & wildlife (1)Water activities (7)Travel photography (2)Aerial tours (2)SIM card (35)Visas (7)

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Reviews/Trip Moments

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Reviews:
Guest User2025-12-06
Great tour. Very knowledgeable guide. Highly recommend. I really enjoyed learning so much about the crime history of Chicago.
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Reviews: The Chicago Theatre Tour Experience
Guest User2026-10-11
We enjoyed our tour very much! Our child wants to study design and production so whenever we travel we always look to see if there are any theater tours. The Chicago Theater tour was a great choice. I loved that we were able to walk around without anyone there. You don't really get to enjoy the architecture as much when you're there to see a show and there are so many people milling around. Our two guides were wonderful. They worked well together and shared so much fun history about the theater. It was fun being able to sit in the different types of seating they had there. There are a lot of stairs so it may not be the best tour for those who struggle with that. We also liked going to parts of the theater that you normally don't get to see. The only downside was because they had a show that night we couldn't go through all of the backstage area, which is the part our child likes to see.
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Reviews: Chicago: Mob and Crime Bus Tour
Guest User2026-10-26
We had a fabulous time on our tour. Sofia was so knowledgeable and super entertaining. She told us all about the different Crime events in Chicago's history. The whole experience was exceptional!! 10 out of 10!! I loved seeing the places where the crimes occurred. Definitely a must do when in Chicago!!!
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Reviews: Chicago to Milwaukee: 1-Day City Highlights w/Miller Brewery
Guest User2026-10-04
Michael was an exceptional guide He was so polite, present and so generous with his time and knowledge I sustained and injury on the trip and he did nothing but look after me and my family The museum and the brewery was amazing Loved food recommendations at the market also A real highlight of our trip

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