Things to Do in Chicago
Discover 70 Day tours in Chicago on Trip.com, updated February 28, 2026, with experiences lasting from 1 to 7 hours. Find the perfect adventure for your day!
From SGD 34.77 per person, with an average total of SGD 92.86. Choose the option that suits your plan.
With 14.082k verified reviews, Day tours Chicago boast an average rating of 4.7.
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 Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters", a 2-hour adventure in Chicago!
The next available day tour departs on March 1, 2026. Book now to secure your spot!
Chicago Day tours usually take about 2 hours — perfect for a relaxed, immersive experience!
97% of Chicago Day tours now offer English-speaking guides
February 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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70 results for Chicago Day tours
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Recommended
Duration: 2–2.5 hrsEnglish4.8/5Very good· 18 reviews5% offLimited-time saleFromS$ 101.98S$ 107.35
Duration: 2 hrsEnglish4.9/5Excellent· 214 reviews5% offLimited-time saleFromS$ 43.13S$ 45.41
Duration: 90 minsEnglish4.7/5Very good· 4.3k reviews· 172 bookedFromS$ 55.65
Duration: 45 minsEnglish4.7/5Very good· 1.4k reviews· 203 bookedFromS$ 35.41
Duration: 2 hrsEnglish5.0/5Excellent· 8 reviews5% offLimited-time saleFromS$ 42.12S$ 44.34
FromS$ 635.60
Duration: 2–3 hrsEnglish5.0/5Excellent· 2 reviews5% offLimited-time saleFromS$ 46.93S$ 49.41
Duration: 3 hrsEnglish4.9/5Excellent· 313 reviewsFromS$ 107.49
5% offLimited-time saleFromS$ 101.08S$ 106.41
Duration: 1–1.5 hrsEnglish4.9/5Excellent· 67 reviews5% offLimited-time saleFromS$ 46.93S$ 49.41
5% offLimited-time saleFromS$ 50.54S$ 53.21
Duration: 2 hrsEnglish4.9/5Excellent· 1.5k reviewsFromS$ 44.27
Duration: 4.5 hrsEnglish5.0/5Excellent· 18 reviews5% offLimited-time saleFromS$ 107.21S$ 112.86
Duration: 2–4 hrsEnglish4.9/5Excellent· 11 reviews5% offLimited-time saleFromS$ 58.90S$ 62.01
Duration: 4 hrsEnglishFromS$ 202.17
FromS$ 56.91
Duration: 1.5 hrsEnglish4.9/5Excellent· 7 reviewsFromS$ 85.38
Duration: 75 minsEnglish4.2/5Good· 5 reviewsFromS$ 78.21
FromS$ 81.47
5% offLimited-time saleFromS$ 54.15S$ 57
5% offLimited-time saleFromS$ 40.48S$ 42.62
FromS$ 56.82
FromS$ 41.04
5% offLimited-time saleFromS$ 42.95S$ 45.22
FromS$ 107.32
Duration: 90 minsEnglish4.8/5Very good· 569 reviewsFromS$ 45.25
Duration: 5.7 hrsEnglish4.5/5Satisfied· 4 reviewsFromS$ 189.40
Duration: 3 hrsEnglish5.0/5Excellent· 17 reviews5% offLimited-time saleFromS$ 101.88S$ 107.25
5% offLimited-time saleFromS$ 58.73S$ 61.83
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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: 2-Hour Kayak Rental from North RockwellLake Michigan & Chicago River: 1.5-Hr Sightseeing CruiseSmall-Group Tour of Chicago Neighborhoods: North and South SideCity Cruises Chicago: Brunch, Lunch, or Dinner River CruiseChicago: 48-hour Hop-on Hop-off Tour and 360 CHICAGO DeckChicago: Food and Prohibition Architecture Guided TourChicago Crime and Mob Bus Tour Chicago: Downtown Guided Donut Tasting TourChicago round-trip|Dubuque Town + Galena Town + Grant ParkChicago: Architecture Boat Tour with DrinksChicago: 2-Hour Downtown Kayak RentalChicago: 45 Minute Architectural Sightseeing CruiseThe Art Institute of Chicago: Skip The Line Ticket + Exclusive Guided TourLake Michigan Skyline Cruise in ChicagoMedieval Torture Museum Ticket with Audio Guide and Ghost Hunting
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Reviews: City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise
Guest User2026-02-02
Great experience, receiving a voucher due to us not being able to go out. But just the experience, food, staff and captain were amazing! Our server Jamie gave us the best experience. We will be visiting again in the summer!★
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Reviews: Chicago: Secret Interiors Architecture Walking Tour
Guest User2026-02-16
The tour was incredibly fun!!! Our guide, Annie, has an unbelievable amount of detailed knowledge; I learned so much about the wonderful city of Chicago! The two hours were packed with new impressions of the city's history and architecture. I highly recommend it!!!★
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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's Original Dazzling Architectural Interiors Tour
Guest User2025-12-24
Spencer is amazing! so knowledgeable and a true chicagonean. I love all the stops, truly beautiful
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