Top picks for Chicago Day tours
Discover 116 Day tours in Chicago on Trip.com, updated December 29, 2025, with experiences lasting from 1 to 9 hours. Find the perfect adventure for your day!
From JPY 4,383.00 per person, with an average total of JPY 11,140.35. Choose the option that suits your plan.
With 12.202k 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 4.345k reviews and a 4.7 rating.
Now on Trip.com: "Chicago Favorites Ultimate Food and Walking Tour ", a 3-hour adventure in Chicago!
The next available day tour departs on December 30, 2025. Book now to secure your spot!
Chicago Day tours usually take about 3 hours — perfect for a relaxed, immersive experience!
100% 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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116 results for Chicago Day tours
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Recommended
91.4% of travelers recommendDuration: 90–120 minsEnglishFree cancellationBook now for today4.7/5Great· 1.6k reviewsFromJPY 7,670
92.2% of travelers recommendDuration: 90 minsEnglishFree cancellationBook now for today4.7/5Great· 4.3k reviews· 161 bookedFromJPY 7,043
24 consecutive positive reviewsDuration: 45 minsEnglishFree cancellationBook now for today4.7/5Great· 1.4k reviews· 183 bookedFromJPY 4,383
Duration: 1 hrEnglish5.0/5Excellent· 1 reviewFromJPY 7,942
35 consecutive positive reviewsDuration: 3 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 1.9k reviewsFromJPY 13,302
81 consecutive positive reviewsDuration: 2 hrsEnglishFree cancellation4.9/5Excellent· 376 reviewsFromJPY 7,505
44 consecutive positive reviewsDuration: 2–4 hrsEnglishFree cancellation4.8/5Great· 682 reviewsFromJPY 7,662
28 consecutive positive reviewsDuration: 30 minsEnglishFree cancellationBook now for today4.8/5Great· 92 reviews5% offLimited-time saleFromJPY 5,652JPY 5,950
Discover the traditions, symbols, and stories behind Chinatown's rich heritage.Duration: 3 hrsEnglishFree cancellationBook now for today5.0/5Excellent· 16 reviews5% offLimited-time saleFromJPY 12,635JPY 13,300
Admire the towering Willis Tower and the Civic Opera BuildingDuration: 1.5 hrsEnglishFree cancellation4.0/5Good· 3 reviews5% offLimited-time saleFromJPY 8,669JPY 9,126
Duration: 270 minsEnglishFree cancellation4.5/5Excellent· 48 reviewsFromJPY 19,564
79 consecutive positive reviewsDuration: 3 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 313 reviewsFromJPY 13,617
Explore Chicago through iconic film and television locations set among dramatic skylines and historic landmarks.Duration: 5.6 hrsEnglishFree cancellationFromJPY 18,469
Explore Chicago's iconic architecture on foot,Duration: 4.5 hrsEnglishFree cancellation5.0/5Excellent· 18 reviews5% offLimited-time saleFromJPY 14,717JPY 15,492
Chicago's Architecture, Culture and HistoryDuration: 2.5 hrsEnglishFree cancellation5.0/5Excellent· 2 reviews5% offLimited-time saleFromJPY 7,721JPY 8,128
91% of travelers recommendDuration: 90 minsEnglishFree cancellation4.6/5Excellent· 1k reviewsFromJPY 7,043
FromJPY 14,085
76 travelers savedDuration: 5.7 hrsEnglishFree cancellation4.5/5Excellent· 4 reviewsFromJPY 23,477
26 consecutive positive reviewsDuration: 2 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 333 reviewsFromJPY 5,478
Stroll through the charming old towns of Iowa and admire the enchanting riverfront scenery.Duration: 9 hrsEnglishFree cancellationFromJPY 16,173
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Trip.com Picks
Popular Chicago Tours
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Chicago: Chinatown Food & Culture Walking TourChicago River 45-Minute Architecture Tour from Magnificent Mile'Spray Paint & Sip' urban art workshop in ChicagoChicago: Loop Neighborhood Guided Walking TourChicago: Field Museum of Natural History Ticket or VIP TourOriginal Chicago Prohibition TourMillennium Park self-guided walking audio tour in ChicagoChicago: Moonlight Paddle Tour on the Chicago RiverChicago: Museum of Ice Cream Entry TicketChicago River 90-Minute Architecture TourChicago: Highlights & Attractions Walking TourScenic Chicago Night TourBite into Chicago: Discover the City’s Most Iconic FoodChicago: 2-Hour Kayak Rental from BridgeportChicago Favorites Ultimate Food and Walking Tour
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Reviews: Chicago Crime and Mob Bus Tour
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 River 90-Minute Architecture Tour
Guest User2025-12-17
It was really, really great ㅠ The highlight of my trip to Chicago.. This is almost 80% of my memories of Chicago and I have no regrets. The buildings are really big and pretty. Make memories.★
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Reviews: Chicago River 45-Minute Architecture Tour from Magnificent Mile
Guest User2024-10-07
Beautiful views! Very informative. So many fun facts you will learn. We definitely recommend when you’re in Chicago. Staff did a great job. Thank you!★
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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 ★
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Reviews: Chicago Favorites Ultimate Food and Walking Tour
Guest User2025-12-14
Gabe was a terrific guide through the streets of town and wonderful bites along with great tidbits of history and holiday festivities!★
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Reviews: Chicago City Minibus Tour
Guest User2025-10-28
learn alot about chicago history and cultural influences on arcitecture. would have like to visit inside of some of the other places mention.
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