Top Chicago Day Tours
Discover 99 Day tours in Chicago on Trip.com, updated February 27, 2026, with experiences lasting from 1 to 8 hours. Find the perfect adventure for your day!
From SGD 34.77 per person, with an average total of SGD 90.41. Choose the option that suits your plan.
With 13.338k 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: "Art Institute of Chicago Private Expert Guided Tour", a 2-hour adventure in Chicago!
The next available day tour departs on February 28, 2026. Book now to secure your spot!
Chicago Day tours usually take about 2 hours — perfect for a relaxed, immersive experience!
100% of Chicago Day tours now offer English-speaking guides
February 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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99 results for Chicago Day tours
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Recommended
Duration: 270 minsEnglish4.5/5Satisfied· 48 reviewsFromSGD 158.02
Duration: 2–4 hrsEnglish4.9/5Excellent· 11 reviews5% offLimited-time saleFromSGD 58.71SGD 61.81
Duration: 45 minsEnglish4.7/5Very good· 1.4k reviews· 203 bookedFromSGD 35.40
Duration: 90 minsEnglish4.7/5Very good· 4.3k reviews· 172 bookedFromSGD 55.63
5% offLimited-time saleFromSGD 36.05SGD 37.95
5% offLimited-time saleFromSGD 70.75SGD 74.48
Duration: 2–2.5 hrsEnglish4.8/5Very good· 18 reviews5% offLimited-time saleFromSGD 101.64SGD 106.99
Duration: 2 hrsEnglish4.9/5Excellent· 214 reviews5% offLimited-time saleFromSGD 43.12SGD 45.39
Duration: 2 hrsEnglish4.9/5Excellent· 1.5k reviewsFromSGD 44.25
5% offLimited-time saleFromSGD 95.04SGD 100.05
Duration: 2–3 hrsEnglish5.0/5Excellent· 2 reviews5% offLimited-time saleFromSGD 46.77SGD 49.24
5% offLimited-time saleFromSGD 34.77SGD 36.61
5% offLimited-time saleFromSGD 42.97SGD 45.24
Duration: 1.5 hrsEnglish5.0/5Excellent· 1 review5% offLimited-time saleFromSGD 163.40SGD 172.01
Duration: 2.5 hrsEnglish5.0/5Excellent· 2 reviews5% offLimited-time saleFromSGD 62.50SGD 65.79
FromSGD 107.45
Duration: 5.7 hrsEnglish4.5/5Satisfied· 4 reviewsFromSGD 189.63
Duration: 2.5 hrsEnglish5.0/5Excellent· 11 reviews5% offLimited-time saleFromSGD 108.07SGD 113.76
Duration: 45–120 minsEnglish4.2/5Good· 81 reviewsFromSGD 40.44
FromSGD 63.18
FromSGD 58.02
Duration: 90 minsEnglish4.8/5Very good· 569 reviewsFromSGD 46.20
Duration: 3 hrsEnglish5.0/5Excellent· 17 reviews5% offLimited-time saleFromSGD 103.98SGD 109.46
FromSGD 58.02
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Reviews/Trip Moments
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Reviews: Small-Group Tour of Chicago Neighborhoods: North and South Side
Guest User2025-11-05
An authentic tour experience from a guide who loves Chicago. You will learn a lot and be entertained. ★
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Reviews: Chicago: City Minibus Tour with Optional Architecture Cruise
Guest User2025-10-13
Avery was very knowledgeable and he shared his information with everyone on the tour. I would consider taking this tour again.★
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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 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: The Chicago Theatre Tour Experience
Guest User2026-01-18
If in Chicago, make sure you go this tour - what a great experience. The tour guides (Jackie and the team member (sorry didn't get the name) were outstanding. So much history at The Chicago - well worth it !
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