Top picks for Chicago Tours
Discover 57 Tours in Chicago on Trip.com, updated February 25, 2026, with experiences lasting from 1 to 8 hours. Find the perfect adventure for your day!
From SGD 35.46 per person, with an average total of SGD 96.78. Choose the option that suits your plan.
With 7.215k verified reviews, Tours Chicago boast an average rating of 4.8.
This week's most popular 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 26, 2026. Book now to secure your spot!
Chicago Tours usually take about 2 hours — perfect for a relaxed, immersive experience!
60% of Chicago Tours now offer English-speaking guides
February is the perfect time to visit Chicago! Choose from 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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57 results for Chicago Tours
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Free cancellationBook now for todayDuration: 2 hrsFromSGD 62.64
91.8% of travelers recommendFree cancellationBook now for todayDuration: 45 mins4.7/5Very good· 1.4k reviews· 203 bookedFromSGD 35.46
92.2% of travelers recommendFree cancellationBook now for todayDuration: 90 mins4.7/5Very good· 4.3k reviews· 172 bookedFromSGD 55.72
Chicago Shoreline Cruise Admission (Included in Price)Free cancellationDuration: 4 hrs5.0/5Excellent· 3 reviewsFromSGD 239.42
Create memories at 3 amazing photo stops, including one of the Chicago skylineFree cancellationBook now for todayDuration: 2–4 hrs4.9/5Excellent· 11 reviews5% offLimited-time saleFromSGD 58.89SGD 61.99
Free cancellationDuration: 270 mins4.5/5Satisfied· 48 reviewsFromSGD 158.30
Behold the beautiful architecture of the Museum CampusFree cancellationDuration: 3 hrs4.9/5Excellent· 9 reviews5% offLimited-time saleFromSGD 70.99SGD 74.73
Free cancellationBook now for todayDuration: 3 hrsFromSGD 101.44
Free cancellationDuration: 90 minsFromSGD 37.89
Free cancellationDuration: 2 hrsFromSGD 61.87
Creative cocktails, wine, and beer from our fully-stocked cash barFree cancellationDuration: 2–2.5 hrs4.8/5Very good· 18 reviews5% offLimited-time saleFromSGD 113.46SGD 119.44
Explore the birthplace of an American icon through legendary motorcycles and immersive exhibits at the Harley Davidson MuseumFree cancellationDuration: 8 hrsFromSGD 158.30
Free cancellationBook now for todayDuration: 4 hrsFromSGD 163.33
Explore Midtown landmarks including Rockefeller Center and Times SquareFree cancellationDuration: 1 day5.0/5Excellent· 1 review5% offLimited-time saleFromSGD 210.54SGD 221.63
90.2% of travelers recommendFree cancellationBook now for todayEnglish4.6/5Satisfied· 92 reviews5% offLimited-time saleFromSGD 54.14SGD 56.99
Free cancellationDuration: 30–45 mins4.5/5Satisfied· 246 reviewsFromSGD 41.16
Free cancellationDuration: 90 minsFromSGD 58.08
Free cancellationDuration: 90 minsFromSGD 63.14
Discover the secrets of the universe at Adler Planetarium, and more!Free cancellationEnglish4.7/5Very good· 13 reviews5% offLimited-time saleFromSGD 95.04SGD 100.05
28 consecutive positive reviewsFree cancellationBook now for todayDuration: 1–1.5 hrs4.9/5Excellent· 67 reviews5% offLimited-time saleFromSGD 46.93SGD 49.4
97.2% of travelers recommendFree cancellationBook now for todayDuration: 90 mins4.8/5Very good· 569 reviewsFromSGD 45.38
Enter the museum 30 minutes before public opening hoursFree cancellationDuration: 2.5 hrs5.0/5Excellent· 11 reviews5% offLimited-time saleFromSGD 108.41SGD 114.12
Challenge your friends or family to a round of mini golf on the Putt-Putt courseFree cancellationBook now for todayDuration: 1.5 hrs4.4/5Good· 47 reviews5% offLimited-time saleFromSGD 40.64SGD 42.78
90.9% of travelers recommendFree cancellationDuration: 1.5 hrs4.7/5Very good· 44 reviews5% offLimited-time saleFromSGD 50.54SGD 53.2
Enjoy a fast entry process with a ticket that lets you skip the ticket officeFree cancellationDuration: 30 mins4.7/5Very good· 11 reviews5% offLimited-time saleFromSGD 39.11SGD 41.17
Admire Art Deco, Beaux-Arts, and neoclassical architecture.Free cancellationDuration: 2–3 hrs5.0/5Excellent· 2 reviews5% offLimited-time saleFromSGD 46.93SGD 49.4
29 consecutive positive reviewsFree cancellationBook now for todayDuration: 2 hrs4.9/5Excellent· 255 reviews5% offLimited-time saleFromSGD 44.34SGD 46.68
FromSGD 154.49
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Reviews/Trip Moments
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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: Chicago Highlights Walking Tour with Skydeck & Cruise
Guest User2025-04-14
The tour was excellent Andrew did a wonderful job. He was very knowledgeable about Chicago history the buildings. Both experiences the sky deck, and the boat were great too. Highly recommend the tour just make sure to wear warm coat and comfortable shoes.Trip.com Picks
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