Top Chicago Day Tours

Discover 137 Day tours in Chicago on Trip.com, updated November 13, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From $1.11 per person, with an average total of $87.30. Choose the option that suits your plan.

With 7.461k 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 November 14, 2026. Book now to secure your spot!

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

50% of Chicago Day tours now offer English-speaking guides

November is the perfect time to visit Chicago! Choose from 137 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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137 results for Chicago Day tours

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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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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 River 90-Min Architecture Boat Tour
Guest User2026-10-16
Hello, the tour was very interesting, but our English wasn't good enough to understand the explanations. Perhaps audio guides or a printed or downloadable version could be offered to help people follow and understand the tour. Given the number of tourists in Chicago and on the ship, a French version would certainly be helpful to many French speakers.
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Reviews: Chicago: Downtown Pizza Guided Walking Tour with Tastings
Guest User2026-08-27
The pizza tour was awesome! The pizza selections were delicious, the guide was knowledgeable about not only the pizza, and the restaurants to which we visited, but also about Chicago. He told us about the sites we saw along the way to the restaurants. If I had any negative is it was ALOT of walking. The guide did hold up every once in a while to allow us to catch up, but overall, it was a great tour.
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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.