Top picks for Chicago Day tours
Discover 102 Day tours in Chicago on Trip.com, updated February 20, 2026, with experiences lasting from 1 to 9 hours. Find the perfect adventure for your day!
From JPY 1,683.00 per person, with an average total of JPY 11,515.61. Choose the option that suits your plan.
With 11.638k 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 Loop District Food Tour with Deep Dish & Beef Sandwich", a 3-hour adventure in Chicago!
The next available day tour departs on February 21, 2026. 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
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.
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102 results for Chicago Day tours
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Recommended
Duration: 3 hrsEnglish4.9/5Excellent· 313 reviewsFromJPY 12,981
Duration: 2–3 hrsEnglish5.0/5Excellent· 2 reviews5% offLimited-time saleFromJPY 5,670JPY 5,969
5% offLimited-time saleFromJPY 11,486JPY 12,091
Duration: 45 minsEnglish4.7/5Very good· 1.4k reviews· 200 bookedFromJPY 4,277
Duration: 1.5 hrsEnglish4.9/5Excellent· 7 reviewsFromJPY 10,336
Duration: 3 hrsEnglishFromJPY 19,176
FromJPY 12,981
Duration: 2–4 hrsEnglish4.9/5Excellent· 11 reviews5% offLimited-time saleFromJPY 7,116JPY 7,491
5% offLimited-time saleFromJPY 8,526JPY 8,975
Duration: 2–2.5 hrsEnglish4.8/5Very good· 17 reviews5% offLimited-time saleFromJPY 13,711JPY 14,433
Duration: 4.5 hrsEnglish5.0/5Excellent· 18 reviews5% offLimited-time saleFromJPY 12,954JPY 13,636
FromJPY 7,651
FromJPY 6,873
Duration: 90 minsEnglish4.7/5Very good· 4.3k reviews· 170 bookedFromJPY 6,720
Duration: 90 minsEnglish4.8/5Very good· 569 reviewsFromJPY 5,473
5% offLimited-time saleFromJPY 5,209JPY 5,484
5% offLimited-time saleFromJPY 6,069JPY 6,389
Duration: 4 hrsEnglishFromJPY 24,212
FromJPY 9,842
FromJPY 6,126
FromJPY 7,484
5% offLimited-time saleFromJPY 7,123JPY 7,498
Duration: 3 hrsEnglish5.0/5Excellent· 17 reviews5% offLimited-time saleFromJPY 12,356JPY 13,007
Duration: 1 hrEnglish5.0/5Excellent· 1 reviewFromJPY 7,640
Duration: 150 minsEnglishFromJPY 8,449
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Reviews/Trip Moments
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Reviews: Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Guest User2024-07-19
Sue was an excellent guide and host…highly recommend. In addition to the food knowledge, Sue showed us some great architectural and unique information about the great city of Chicago.★
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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 Explorer Pass: 2 to 7 Attractions including SkyDeck
Guest User2025-11-22
The best way to discover the city through various attractions at a discounted price!★
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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: Historic Architecture Chicago River Small Boat Tour
Guest User2025-10-15
We enjoyed the smaller feel of this tour vs others that have hundreds of people, but we had a hard time hearing the guide. We were at the front of the boat and between the people around us talking nonstop and the low volume of the speaker, we only heard about half of the tour. This wasn’t the guide’s fault, he was humorous and knowledgeable, but it did affect how much we learned while on the cruise. I also highly recommend arriving very early. Instructions said come 15 mins early and we got there 30 mins early to be safe, and almost every single seat was already taken. Overall, I would recommend the tour, just be sure you get there very early so you get a seat in the back where you can hear better.
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