Top Chicago Day Tours

Discover 111 Day tours in Chicago on Trip.com, updated January 6, 2026, with experiences lasting from 1 to 4 hours. Find the perfect adventure for your day!

From AED 85.61 per person, with an average total of AED 213.19. Choose the option that suits your plan.

With 13.279k verified reviews, Day tours Chicago boast an average rating of 4.7.

This week's most popular Day tours: "Chicago River 90-Minute Architecture Tour", with 4.345k reviews and a 4.7 rating.

Now on Trip.com: "Chicago: City Minibus Tour with Optional Architecture Cruise", a 4-hour adventure in Chicago!

The next available day tour departs on January 7, 2026. Book now to secure your spot!

Chicago Day tours usually take about 4 hours — perfect for a relaxed, immersive experience!

97% of Chicago Day tours now offer English-speaking guides

January is the perfect time to visit Chicago! Choose from Day tours available day tours, including seasonal favorites like Chicago River 90-Minute Architecture 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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111 results for Chicago Day tours

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Reviews/Trip Moments

Reviews: Lake Michigan Sunset Cruise in Chicago
Guest User2025-10-05
The views were amazing and the staff were friendly and entertaining. Would recommend this cruise to other travelers.
Reviews: Chicago: Architecture River Cruise Skip-the-Ticket Line
Guest User2025-10-18
The Puerto Rican tour guide was excellent. We enjoyed the cruise and learning about the different blgs. Liam makes it memorable with her random jokes, a great experience in general. Highly recommended. A different kinda view of Chicago.
Reviews: Chicago: Navy Pier Centennial Wheel Ticket
Guest User2025-12-07
It's a lot of fun, and the atmosphere is very family-friendly. It's definitely a must-do activity if you're in Chicago.
Reviews: Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929
Guest User2025-10-26
very nice view, detailed explanation of buildings of Chicago. I recommend late afternoon or evening time to jump on the cruise
Reviews: Chicago: City Minibus Tour with Optional Architecture Cruise
Guest User2025-10-13
Avery was very knowledgeable and he shared his information with everyone on the tour. I would consider taking this tour again.
Reviews: Chicago Highlights Walking Tour with Skydeck & Cruise
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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