Top Chicago Day Tours

Discover 152 Day tours in Chicago on Trip.com, updated October 23, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From SGD 1.44 per person, with an average total of SGD 96.68. Choose the option that suits your plan.

With 12.087k 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 24, 2026. Book now to secure your spot!

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

46% of Chicago Day tours now offer English-speaking guides

October is the perfect time to visit Chicago! Choose from 152 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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152 results for Chicago Day tours

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RecommendedAttractions (47047)Shows & events (2)Boat experiences (41)Cultural experiences (27)Food & drink (27)Outdoor experiences (2)Day tours (152)Water activities (11)City sightseeing (64)Nature & wildlife (2)Travel photography (4)Aerial tours (3)SIM card (33)Visas (7)Boat tickets (2)

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Reviews/Trip Moments

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Reviews: Chicago: Willis Tower Skydeck and The Ledge Ticket
Guest User2026-10-20
It's definitely worth going up; seeing Chicago from that perspective is spectacular. We went around 5:30 pm, a perfect time, with the sun reflecting off the skyscrapers. A beautiful autumn evening. Buying our tickets here meant we didn't have to wait to take photos on the Skydecker, unlike the other line, which had to wait quite a while. You have 90 minutes to take photos, but that's plenty, and since there weren't many people, we were able to stay longer, so everything was great.
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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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Reviews:
Guest User2025-04-14
The tour was excellent Andrew did a wonderful job. He was very knowledgeable about Chicago history the buildings. Both experiences the sky deck, and the boat were great too. Highly recommend the tour just make sure to wear warm coat and comfortable shoes.

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