Top Chicago Day Tours
Discover 80 Day tours in Chicago on Trip.com, updated December 31, 2025, with experiences lasting from 1 to 9 hours. Find the perfect adventure for your day!
From HKD 85.55 per person, with an average total of HKD 525.44. Choose the option that suits your plan.
With 12.761k verified reviews, Day tours Chicago boast an average rating of 4.8.
This week's most popular Day tours: "Chicago River 90-Minute Architecture Tour", with 4.344k reviews and a 4.7 rating.
Now on Trip.com: "Chicago: Classic Food & Walking Tour with Free Bike or Kayak", a 3-hour adventure in Chicago!
The next available day tour departs on January 1, 2026. Book now to secure your spot!
Chicago Day tours usually take about 3 hours — perfect for a relaxed, immersive experience!
58% of Chicago Day tours now offer English-speaking guides
December 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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80 results for Chicago Day tours
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Includes FREE 2-hour bike or kayak rental to extend your Chicago adventure.Duration: 3 hrsEnglishFree cancellation5.0/5Excellent· 4 reviews5% offLimited-time saleFromHK$627.48HK$660.51
95.9% of travelers recommendDuration: 2 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 246 reviews5% offLimited-time saleFromHK$272.15HK$286.48
26 consecutive positive reviewsDuration: 1 hrEnglish5.0/5Excellent· 26 reviews5% offLimited-time saleFromHK$221.48HK$233.14
Explore Chicago's iconic architecture on foot,Duration: 4.5 hrsEnglishFree cancellation5.0/5Excellent· 18 reviews5% offLimited-time saleFromHK$731.00HK$769.48
Admire Art Deco, Beaux-Arts, and neoclassical architecture.Duration: 2–3 hrsEnglishFree cancellation5.0/5Excellent· 2 reviews5% offLimited-time saleFromHK$287.97HK$303.13
Hear fascinating stories of Chicago's history, art, & cultureEnglishFree cancellationBook now for today4.4/5Good· 5 reviewsFromHK$652.92
35 consecutive positive reviewsDuration: 3 hrsEnglishFree cancellation4.9/5Excellent· 1.9k reviewsFromHK$661.31
Chicago Shoreline Cruise Admission (Included in Price)Duration: 4 hrsEnglishFree cancellation5.0/5Excellent· 3 reviews5% offLimited-time saleFromHK$1,395.59HK$1,469.05
Duration: 1 hrEnglish5.0/5Excellent· 1 reviewFromHK$389.17
FromHK$350.29
Duration: 45 mins4.7/5Great· 1.4k reviews· 173 bookedFromHK$217.96
5% offFromHK$353.28HK$371.88
FromHK$272.45
FromHK$381.04
Duration: 90 minsSpanish4.8/5Great· 569 reviewsFromHK$278.91
Duration: 5 hrs4.9/5Excellent· 1.1k reviewsFromHK$785.81
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Reviews: Chicago: Classic Food & Walking Tour with Free Bike or Kayak
Guest User2025-09-25
Our guide Jeff was incredibly knowledgeable, not only about the food we tried but about the history of the city, as well as the architecture. Jeff kept things moving and very upbeat throughout! I would rate Jeff as a five star guide! My husband and I just finished a two week tour of Greece and had many great guides during that time but Jeff was by far the best! Thank you Jeff from Rob and Shannon.★
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Reviews: Chicago: Gangsters and Ghosts Guided Walking Tour
Guest User2025-12-11
Our guide Sophie brought the stories to life. We had a lot of fun. The tour was interesting, and we learned a great deal about Al Capone and his schemes, as well as about tragic lake and theater fires. The tour is highly recommended.★
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Reviews: The Chicago Theatre Tour Experience
Guest User2025-11-24
Our tour guide Jackie was awesome! She was very knowledgeable about the theater even working there. She made it very engaging and informative and was beyond our expectations!★
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Reviews: Chicago in a Day: Food, History & Architecture Walking Tour
Guest User2025-11-20
Exciting and entertaining right to the end. Rich has a lot to say and answered all questions. This tour of Chicago's culinary highlights is 100% recommended for every European!★
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Reviews: Chicago: Magnificent Mile Tour With Optional 360 Chicago
Guest User2025-06-18
Our Mag Mile Tour was great. We learned about the architecture of buildings, design details and history of the area. Our guide Ben was knowledgeable, friendly, full of facts and anecdotes. It was a perfect distance - enough to see the major sites without being too long. We followed with the 360 Chicago at the Hancock. Great tour would highly recommend.★
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Reviews: Chicago: 360 CHICAGO & Big Bus Hop-on Hop-off Tour
Guest User2025-09-16
The bus hit all of the places we wanted to see. It arrived every half hour and any stop which was very convenient.
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