Top picks for Chicago Day tours
Discover 116 Day tours in Chicago on Trip.com, updated January 14, 2026, with experiences lasting from 1 to 9 hours. Find the perfect adventure for your day!
From JPY 4,291.00 per person, with an average total of JPY 11,953.75. Choose the option that suits your plan.
With 14.384k 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 City Day Tour", a 5-hour adventure in Chicago!
The next available day tour departs on January 15, 2026. Book now to secure your spot!
Chicago Day tours usually take about 5 hours — perfect for a relaxed, immersive experience!
100% 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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116 results for Chicago Day tours
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76 travelers savedDuration: 5.7 hrsEnglishFree cancellation4.5/5Satisfied· 4 reviewsFromJPY 23,868
Behold the beautiful architecture of the Museum CampusDuration: 3 hrsEnglishFree cancellation4.9/5Excellent· 9 reviews5% offLimited-time saleFromJPY 8,899JPY 9,368
Admire Art Deco, Beaux-Arts, and neoclassical architecture.Duration: 2–3 hrsEnglishFree cancellationBook now for today5.0/5Excellent· 2 reviewsFromJPY 6,193
Chicago's Architecture, Culture and HistoryDuration: 2.5 hrsEnglishFree cancellation5.0/5Excellent· 2 reviews5% offLimited-time saleFromJPY 6,269JPY 6,599
Enter the museum 30 minutes before public opening hoursDuration: 2.5 hrsEnglishFree cancellation5.0/5Excellent· 11 reviews5% offLimited-time saleFromJPY 10,872JPY 11,445
Duration: 150 minsEnglishFree cancellationFromJPY 14,309
23 consecutive positive reviewsDuration: 2 hrsEnglishFree cancellation4.9/5Excellent· 1.5k reviewsFromJPY 5,570
Explore unknown beautiful spaces that even locals walk by every dayDuration: 2 hrsEnglishFree cancellation5.0/5Excellent· 8 reviews5% offLimited-time saleFromJPY 5,280JPY 5,558
FromJPY 62,851
Create memories at 3 amazing photo stops, including one of the Chicago skylineDuration: 2–4 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 11 reviews5% offLimited-time saleFromJPY 7,384JPY 7,773
98.1% of travelers recommendDuration: 2 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 210 reviews5% offLimited-time saleFromJPY 5,406JPY 5,691
Explore Chicago's iconic architecture on foot,Duration: 4.5 hrsEnglishFree cancellationBook now for today5.0/5Excellent· 18 reviews5% offLimited-time saleFromJPY 14,934JPY 15,720
48-hour hop-on hop-off bus tour covering Chicago's top landmarksEnglishFree cancellationBook now for today4.4/5Good· 5 reviews5% offLimited-time saleFromJPY 12,671JPY 13,338
Duration: 150 minsEnglishFree cancellationFromJPY 13,364
FromJPY 4,291
91.4% of travelers recommendDuration: 90–120 minsEnglishFree cancellation4.7/5Very good· 1.6k reviewsFromJPY 7,797
Explore Chicago's iconic riverfront skyscrapers and historic bridgesDuration: 1.8 hrsEnglishFree cancellationFromJPY 7,638
Chicago Shoreline Cruise Admission (Included in Price)Duration: 4 hrsEnglishFree cancellation5.0/5Excellent· 3 reviewsFromJPY 30,010
Includes FREE 2-hour bike or kayak rental to extend your Chicago adventure.Duration: 3 hrsEnglishFree cancellationBook now for today5.0/5Excellent· 5 reviews5% offLimited-time saleFromJPY 12,820JPY 13,495
One of America's largest art museums, the Milwaukee Art Museum features pristine white architecture with a distinctive design, its roof resembling a bird's wings stretching toward the sky.Duration: 7.6 hrsEnglishFree cancellationFromJPY 18,918
Stroll through the charming old towns of Iowa and admire the enchanting riverfront scenery.Duration: 9 hrsEnglishFree cancellationFromJPY 16,442
21 consecutive positive reviewsDuration: 2 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 247 reviews5% offLimited-time saleFromJPY 5,559JPY 5,852
Get a private link to a curated webpage with historical images and moreDuration: 1.5 hrsEnglishFree cancellation5% offLimited-time saleFromJPY 6,034JPY 6,352- Immerse yourself in Chicago's culture as you explore its vibrant neighborhoodsDuration: 3 hrsEnglishFree cancellation4.9/5Excellent· 14 reviewsFromJPY 9,368
91.2% of travelers recommendEnglishFree cancellation4.6/5Satisfied· 91 reviews5% offLimited-time saleFromJPY 6,787JPY 7,145
92.2% of travelers recommendDuration: 90 minsEnglishFree cancellationBook now for today4.7/5Great· 4.3k reviews· 155 bookedFromJPY 7,043
24 consecutive positive reviewsDuration: 45 minsEnglishFree cancellation4.7/5Great· 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
79 consecutive positive reviewsDuration: 3 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 313 reviewsFromJPY 13,617
Discover the traditions, symbols, and stories behind Chinatown's rich heritage.Duration: 3 hrsEnglishFree cancellationBook now for today4.8/5Great· 19 reviews5% offLimited-time saleFromJPY 12,635JPY 13,301
91% of travelers recommendDuration: 90 minsEnglishFree cancellation4.6/5Excellent· 1k reviewsFromJPY 7,043
28 consecutive positive reviewsDuration: 30 minsEnglishFree cancellationBook now for today4.8/5Great· 92 reviews5% offLimited-time saleFromJPY 5,654JPY 5,952
81 consecutive positive reviewsDuration: 2 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 376 reviewsFromJPY 7,505
44 consecutive positive reviewsDuration: 2–4 hrsEnglishFree cancellationBook now for today4.8/5Great· 682 reviewsFromJPY 7,662
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
Explore Chicago through iconic film and television locations set among dramatic skylines and historic landmarks.Duration: 5.6 hrsEnglishFree cancellationFromJPY 18,469
FromJPY 14,085
Duration: 270 minsEnglishFree cancellationBook now for today4.5/5Excellent· 48 reviewsFromJPY 19,564
26 consecutive positive reviewsDuration: 90 minsEnglishFree cancellation4.6/5Excellent· 433 reviewsFromJPY 7,043
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Millennium Park self-guided walking audio tour in Chicago'Spray Paint & Sip' urban art workshop in ChicagoOriginal Chicago Prohibition TourChicago: Field Museum of Natural History Ticket or VIP TourChicago: Loop Neighborhood Guided Walking TourChicago: Highlights & Attractions Walking TourChicago River 45-Minute Architecture Tour from Magnificent MileChicago: Guided Highlights Tour + SkyDeck + Architecture CruiseChicago: 2-Hour Kayak Rental from BridgeportChicago: Architecture River Cruise from Michigan AvenueChicago: Museum of Ice Cream Entry TicketChicago Loop District Food Tour with Deep Dish & Beef SandwichChicago: Moonlight Paddle Tour on the Chicago RiverChicago River 90-Minute Architecture TourChicago Favorites Ultimate Food and Walking Tour
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Reviews: Chicago City Day Tour
Guest User2024-07-02
The master is super nice, punctual and kind. The experience is great, overall it is great, the service is very good and the price is high.★
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Reviews: Chicago: Ultimate City Attractions Bike Tour
Guest User2025-09-15
Amazing guide and tour. Bikes were excellent and gave us chance to see so much of the city you wouldn’t access on any other tour. Loved it!!★
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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: Art of a City, Downtown Chicago Guided Walking Tour
Guest User2025-08-01
Mandy our tour guide was excellent. Very knowledgeable about the city and its history. Her enthusiasm was impressive and helped to make the tour that much better. Highly recommend this tour with Mandy★
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Reviews: Chicago: Art Institute Skip-the-Line Tour with Guide
Guest User2025-09-01
Our guide was very knowledgeable and did a wonderful job curating a set of important pieces in the time we had. Megan M. delivered great information and with enthusiasm and also allowed time for questions.
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