Top picks for Chicago Day tours

Discover 151 Day tours in Chicago on Trip.com, updated October 21, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From CAD 1.58 per person, with an average total of CAD 108.12. Choose the option that suits your plan.

With 15.987k verified reviews, Day tours Chicago boast an average rating of 4.8.

This week's most popular Day tours: "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 October 22, 2026. Book now to secure your spot!

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

60% of Chicago Day tours now offer English-speaking guides

October is the perfect time to visit Chicago! Choose from 151 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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151 results for Chicago Day tours

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Day tours

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RecommendedAttractions (47072)Boat experiences (38)Shows & events (2)Cultural experiences (27)Day tours (151)Food & drink (27)Outdoor experiences (2)City sightseeing (64)Nature & wildlife (2)Water activities (11)Travel photography (4)Aerial tours (3)SIM card (35)Boat tickets (2)Visas (7)

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Reviews/Trip Moments

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Reviews: Chicago: Willis Tower Skydeck and The Ledge Ticket
Guest User2026-10-18
The Willis Tower is a must see when visiting Chicago. They are good at moving people through the process of getting to the top. We were able to take as much time as we needed and didn’t have to wait too long for our turn on the Ledge. I appreciate that it was limited to 90 seconds per group and there were employees there to move things along and take photos for us. It was a great memory to share with my daughter.
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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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Guest User2025-11-05
An authentic tour experience from a guide who loves Chicago. You will learn a lot and be entertained.
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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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