Top Chicago Activities and Things to Do

Discover 135 Day tour product in Chicago on Trip.com, updated November 4, 2026, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From JPY 1,291 per person, with an average total of JPY 9,938. Choose the option that suits your plan.

With 12.281k verified reviews, Day tour product Chicago boast an average rating of 4.7.

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

Now on Trip.com: "Best of Chicago: Premium Small Group City Tour", a 1-hour adventure in Chicago!

The next available day tour departs on November 5, 2026. Book now to secure your spot!

Chicago Day tour product usually take about 1 hours — perfect for a relaxed, immersive experience!

41% of Chicago Day tour product now offer English-speaking guides

November is the perfect time to visit Chicago! Choose from 135 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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135 results for Chicago Day tour product

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RecommendedAttractions (47314)Shows & events (2)Boat tours (35)Culture & history (56)Food & drink (27)Day tours (139)Outdoor & sports (2)Water activities (7)City sightseeing (60)Nature & wildlife (1)Travel photography (3)Aerial tours (2)SIM card (34)Visas (7)

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Reviews/Trip Moments

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Reviews: Chicago: Willis Tower Skydeck and The Ledge Ticket
Guest User2026-10-26
What an amazing experience. Super cool Staff was very friendly. We were able to get back in line for a second time.
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Reviews: Chicago: City Minibus Tour with Optional Architecture Cruise
Guest User2026-10-15
ALAN WAS FANTABULOUS AT HIGHLIGHTING CHICAGO’s artifacts, history, and landmarks. BEST tour guide EVER! It was a very good tour and I enjoyed every bit of it.
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Guest User2025-11-11
Liked being able to be out on the lake and seeing the Chicago skyline! Everything was well organized.
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Reviews: Chicago Architecture Boat Tour & Hop-on Hop-off Bus Tour
Guest User2026-08-25
The HOHO was perfect! The first stop was across the street from our hotel so that was great, we got off at Navy Pier and had dinner there. Hopped off at Millinium Park to see the “bean” and walked through the park to see other things on display. The architecture boat tour was very good, our Guide talked about the buildings architects and how the buildings became to be. He also told us a bit about the rivers history, very informative.
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Guest User2024-09-13
Every seat on the boat brought exceptional views! The recorded tour guide gave wonderful information and facts about the scenery

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