Top 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 PHP 70.62 per person, with an average total of PHP 5,609.66. Choose the option that suits your plan.

With 12.233k verified reviews, Day tours Chicago boast an average rating of 4.9.

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!

50% 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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RecommendedAttractions (47072)Shows & events (2)Boat experiences (38)Cultural experiences (27)Food & drink (27)Outdoor experiences (2)Day tours (151)Water activities (11)Nature & wildlife (2)City sightseeing (64)Travel photography (4)Aerial tours (3)SIM card (34)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 User2026-10-18
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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Reviews: Chicago: Shoreline Lake Michigan Skyline Cruise
Guest User2026-10-12
Fun--it was a perfect fall sunny day to experience Lake Michigan for 30 minutes and see magnifivent Chicago and the shoreline!
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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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Reviews: Chicago Architecture River Cruise
Guest User2026-04-23
A must do in Chicago! The buildings here are rich in history and architectural meaning.

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Chicago Walking Tour: A Walk Through TimeChicago: Crucero turístico familiar de arquitectura de 45 minutos por el ríoChicago: Offbeat Guided Street Art TourChicago: Willis Tower Skydeck and The Ledge TicketChicago Architecture River CruiseChicago: Tour guiado de donuts por Fulton MarketChicago Architecture & True Crime Tour: Halloween EditionChicago: 90-Minute Architecture Tour on the Lake & RiverChicago: Tour en autobús de la mafia y el crimenTour nocturno de crímenes de ChicagoChicago: Highlights & Attractions Walking TourChicago: Tour Hop-on Hop-off en autobús descubierto con 11 paradasChicago: Downtown Pizza Guided Walking Tour with TastingsThe Art Institute of Chicago: Skip The Line Ticket and Semi-Private Guided TourTour Original de Arquitectura e Interiores de Chicago: Interiores DeslumbrantesChicago SIM CardChicago ActivitiesChicago City PassChicago Shopping DiscountsChicago Airport ServicesChicago Travel ServicesWellness & Spa in ChicagoChicago Connectivity SolutionsChicago Yacht CharterChicago Day ToursChicago Spa & MassageThings to do in ShanghaiThings to do in BeijingThings to do in Hong KongThings to do in OsakaThings to do in ZhangjiajieThings to do in SingaporeThings to do in ChongqingThings to do in TokyoThings to do in GuangzhouThings to do in Xi'anThings to do in ChinaThings to do in JapanThings to do in ThailandThings to do in VietnamThings to do in South Korea