Things to Do in Chicago
Discover 101 Day tours in Chicago on Trip.com, updated January 20, 2026, with experiences lasting from 1 to 7 hours. Find the perfect adventure for your day!
From SGD 34.79 per person, with an average total of SGD 85.64. Choose the option that suits your plan.
With 10.61k 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: Mob and Crime Bus Tour", a 1-hour adventure in Chicago!
The next available day tour departs on January 21, 2026. Book now to secure your spot!
Chicago Day tours usually take about 1 hours — perfect for a relaxed, immersive experience!
97% of Chicago Day tours now offer English-speaking guides
January is perfect for visiting Chicago! Choose from Day tours available day tours, including seasonal hits 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.
Explore Chicago! Visit top attractions and enjoy fun activities. From city tours to cultural spots, there's so much to do in this lively city. Don't miss out on the amazing experiences.
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101 results for Chicago Day tours
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91.4% of travelers recommendDuration: 90–120 minsEnglishFree cancellation4.7/5Very good· 1.6k reviewsFromS$ 62.95
97% of travelers recommendDuration: 30 minsEnglishFree cancellationBook now for today4.8/5Very good· 99 reviews5% offLimited-time saleFromS$ 46.57S$ 49.03
94.3% of travelers recommendDuration: 1.5 hrsEnglishFree cancellation4.7/5Very good· 53 reviews5% offLimited-time saleFromS$ 60.02S$ 63.18
92.2% of travelers recommendDuration: 90 minsEnglishFree cancellation4.7/5Very good· 4.3k reviews· 169 bookedFromS$ 57.81
91.8% of travelers recommendDuration: 45 minsEnglishFree cancellation4.7/5Very good· 1.4k reviews· 195 bookedFromS$ 35.97
Duration: 2 hrsEnglishFree cancellationBook now for todayFromS$ 40.51
76 travelers savedDuration: 5.7 hrsEnglishFree cancellation4.5/5Satisfied· 4 reviewsFromS$ 192.68
Admire Art Deco, Beaux-Arts, and neoclassical architecture.Duration: 2–3 hrsEnglishFree cancellation5.0/5Excellent· 2 reviews5% offLimited-time saleFromS$ 47.77S$ 50.29
79 consecutive positive reviewsDuration: 3 hrsEnglishFree cancellation4.9/5Excellent· 313 reviewsFromS$ 111.76
90.2% of travelers recommendEnglishFree cancellation4.7/5Very good· 41 reviews5% offLimited-time saleFromS$ 35.53S$ 37.4
Explore unknown beautiful spaces that even locals walk by every dayDuration: 2 hrsEnglishFree cancellation5.0/5Excellent· 8 reviews5% offLimited-time saleFromS$ 42.87S$ 45.13
10-hour private charter with Chinese service - private charter only, no shared transfer, no group tours - dedicated one-on-one customer support after bookingDuration: 7.3 hrsMandarinFromS$ 636.37
Discover the secrets of the universe at Adler Planetarium, and more!EnglishFree cancellation4.7/5Very good· 13 reviews5% offLimited-time saleFromS$ 102.90S$ 108.32
Duration: 150 minsEnglishFree cancellationFromS$ 70.53
21 consecutive positive reviewsDuration: 2 hrsEnglishFree cancellationBook now for today4.9/5Excellent· 247 reviews5% offLimited-time saleFromS$ 45.16S$ 47.54
Duration: 2 hrsEnglishFree cancellationBook now for todayFromS$ 63.00
FromS$ 57.99
Create memories at 3 amazing photo stops, including one of the Chicago skylineDuration: 2–4 hrsEnglishFree cancellation4.9/5Excellent· 11 reviews5% offLimited-time saleFromS$ 59.96S$ 63.12
91% of travelers recommendDuration: 90 minsEnglishFree cancellation4.6/5Satisfied· 1k reviewsFromS$ 57.81
FromS$ 34.79
FromS$ 62.85
91.2% of travelers recommendEnglishFree cancellation4.6/5Satisfied· 91 reviews5% offLimited-time saleFromS$ 55.13S$ 58.04
28 consecutive positive reviewsDuration: 1 hrEnglishFree cancellation4.9/5Excellent· 67 reviewsFromS$ 59.08
Explore Chicago's iconic architecture on foot,Duration: 4.5 hrsEnglishFree cancellation5.0/5Excellent· 18 reviews5% offLimited-time saleFromS$ 121.27S$ 127.66
98.1% of travelers recommendDuration: 2 hrsEnglishFree cancellation4.9/5Excellent· 211 reviews5% offLimited-time saleFromS$ 43.90S$ 46.22
Explore Chicago's iconic riverfront skyscrapers and historic bridgesDuration: 1.8 hrsEnglishFree cancellationFromS$ 61.66
Duration: 5 hrsEnglishFree cancellationBook now for todayFromS$ 114.83
26 consecutive positive reviewsDuration: 90 minsEnglishFree cancellation4.6/5Satisfied· 433 reviewsFromS$ 57.81
Creative cocktails, wine, and beer from our fully-stocked cash barDuration: 2–2.5 hrsEnglishFree cancellation4.9/5Excellent· 15 reviews5% offLimited-time saleFromS$ 115.53S$ 121.62
Explore Chicago through iconic film and television locations set among dramatic skylines and historic landmarks.Duration: 5.6 hrsEnglishFree cancellationFromS$ 151.58
Discover horrific instruments of torture, interrogation, and executionEnglishFree cancellation4.7/5Very good· 7 reviews5% offLimited-time saleFromS$ 43.89S$ 46.21
97.2% of travelers recommendDuration: 90 minsEnglishFree cancellationBook now for today4.8/5Very good· 569 reviewsFromS$ 46.03
Discover the traditions, symbols, and stories behind Chinatown's rich heritage.Duration: 3 hrsEnglishFree cancellation5.0/5Excellent· 17 reviews5% offLimited-time saleFromS$ 104.11S$ 109.59
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Your guide to Chicago Day tours
Chicago is a vibrant city with a plethora of activities for visitors. From iconic attractions to unique experiences, there's something for everyone. You can take a day - tour to explore the city's famous landmarks. Visit the Willis Tower for a breathtaking view, or stroll along the Magnificent Mile for some shopping. The city also has numerous museums and art galleries. Whether you're into history, art, or just having fun, Chicago has it all. Come and indulge in the various in - Chicago things to do.
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Chicago: Inside Walking Tour Of Fine Arts BuildingChicago: Art Institute Skip-the-Line Tour with GuideOriginal Chicago Prohibition TourChicago Lake and River Architecture TourChicago 1-day tour: Millennium Park + Cloud Gate + Navy Pier + Magnificent MileChicago: Hop-on Hop-off Sightseeing Tour by Open-top BusThe Chicago Theatre Tour ExperienceChicago: Architecture River Cruise from Michigan AvenueChicago: Downtown Guided Donut Tasting TourChicago private charter tour: Millennium Park + Picasso + Magnificent Mile + Holy Name CathedralChicago: The Loop Guided TourChicago: Architecture Boat Tour with DrinksChicago Highlights Walking Tour with Skydeck & CruiseChicago: Chicago Children's Museum Entry TicketChicago: Tapas & Flamenco Dinner in Ukrainian Village
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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: Flyover in Chicago: An Immersive Flying Theatre Experience
Guest User2025-12-21
It was very cool and exciting. I would add more Chicago themed attractions. MJ (Micheal Jordan) is a huge staple in Chicago and he nor the entire South Side was featured. The actual journey was a lot shorter than I expected.★
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Reviews: Chicago: Mob and Crime Bus Tour
Guest User2026-01-10
Lots of information given and the guide made it interesting. The speed of the conversation made it sometimes hard to listen★
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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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