Top picks for Chicago Tours
Discover 57 Tours in Chicago on Trip.com, updated February 28, 2026, with experiences lasting from 1 to 4 hours. Find the perfect adventure for your day!
From SGD 35.41 per person, with an average total of SGD 85.98. Choose the option that suits your plan.
With 8.306k 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: "Chicago: City Minibus Tour with Optional Architecture Cruise", a 4-hour adventure in Chicago!
The next available day tour departs on March 1, 2026. Book now to secure your spot!
Chicago Tours usually take about 4 hours — perfect for a relaxed, immersive experience!
58% 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.
Search attractions or local attractions & tours
Search
Tours
Top Picks
Available Today
Available Tomorrow
57 results for Chicago Tours
Sort by:
Recommended
Create memories at 3 amazing photo stops, including one of the Chicago skylineFree cancellationDuration: 2–4 hrs4.9/5Excellent· 11 reviews5% offLimited-time saleFromSGD 58.85SGD 61.95
Behold the beautiful architecture of the Museum CampusFree cancellationDuration: 3 hrs4.9/5Excellent· 9 reviews5% offLimited-time saleFromSGD 70.91SGD 74.65
Explore Chicago's iconic architecture on foot,Free cancellationDuration: 4.5 hrs5.0/5Excellent· 18 reviews5% offLimited-time saleFromSGD 107.11SGD 112.75
91.8% of travelers recommendFree cancellationDuration: 45 mins4.7/5Very good· 1.4k reviews· 203 bookedFromSGD 35.41
Discover the secrets of the universe at Adler Planetarium, and more!Free cancellationEnglish4.7/5Very good· 13 reviews5% offLimited-time saleFromSGD 94.97SGD 99.97
Explore Chicago's iconic riverfront skyscrapers and historic bridgesFree cancellationDuration: 1.8 hrsFromSGD 60.71
48-hour hop-on hop-off bus tour covering Chicago's top landmarksFree cancellationBook now for todayEnglish4.4/5Good· 5 reviews5% offLimited-time saleFromSGD 100.97SGD 106.29
Admire Art Deco, Beaux-Arts, and neoclassical architecture.Free cancellationDuration: 2–3 hrs5.0/5Excellent· 2 reviews5% offLimited-time saleFromSGD 46.88SGD 49.35
29 consecutive positive reviewsFree cancellationBook now for todayDuration: 2 hrs4.9/5Excellent· 255 reviews5% offLimited-time saleFromSGD 44.31SGD 46.65
Free cancellationDuration: 30–45 mins4.5/5Satisfied· 246 reviewsFromSGD 41.11
28 consecutive positive reviewsDuration: 1 hr5.0/5Excellent· 28 reviews5% offLimited-time saleFromSGD 36.06SGD 37.96
90.2% of travelers recommendFree cancellationBook now for todayEnglish4.6/5Satisfied· 92 reviews5% offLimited-time saleFromSGD 54.09SGD 56.94
92.2% of travelers recommendFree cancellationDuration: 90 mins4.7/5Very good· 4.3k reviews· 172 bookedFromSGD 55.65
Free cancellationBook now for todayDuration: 2 hrsFromSGD 62.77
28 consecutive positive reviewsFree cancellationBook now for todayDuration: 1–1.5 hrs4.9/5Excellent· 67 reviews5% offLimited-time saleFromSGD 46.88SGD 49.35
59 consecutive positive reviewsFree cancellationDuration: 2 hrs4.9/5Excellent· 1.5k reviewsFromSGD 44.27
Free cancellationDuration: 270 mins4.5/5Satisfied· 48 reviewsFromSGD 158.08
23 consecutive positive reviewsFree cancellationDuration: 2 hrs4.9/5Excellent· 214 reviews5% offLimited-time saleFromSGD 43.09SGD 45.36
Admire the architectural grandeur of historic buildings in the LoopFree cancellationDuration: 2 hrs5% offLimited-time saleFromSGD 72.12SGD 75.92
Explore unknown beautiful spaces that even locals walk by every dayFree cancellationDuration: 2 hrs5.0/5Excellent· 8 reviews5% offLimited-time saleFromSGD 42.07SGD 44.29- Immerse yourself in Chicago's culture as you explore its vibrant neighborhoodsFree cancellationDuration: 3 hrs4.9/5Excellent· 14 reviews5% offLimited-time saleFromSGD 70.91SGD 74.65
Free cancellationDuration: 90 minsFromSGD 58.29
Enter the museum 30 minutes before public opening hoursFree cancellationDuration: 2.5 hrs5.0/5Excellent· 11 reviews5% offLimited-time saleFromSGD 108.31SGD 114.02
Free cancellationDuration: 90 minsFromSGD 63.26
Enjoy a smaller historic yacht experience rather than a large shipFree cancellationDuration: 1.5 hrs4.9/5Excellent· 7 reviewsFromSGD 85.50
Exclusive Travel KeepsakesFree cancellationDuration: 1 dayFromSGD 159.43
FromSGD 154.49
View more
Frequently asked questions about Chicago Tours
How many Tours are available in Chicago on Trip.com?
What are the best Tours in Chicago?
What are the top-rated Tours in Chicago?
How can I contact Trip.com customer support?
Can I change or cancel my booking?
How can I get discounted prices?
Trip.com Picks
Popular Chicago Tours
Best Chicago Experiences
Popular Products
Popular activities
More Popular Destinations
Chicago: Loop Neighborhood Guided Walking TourChicago River 45-Minute Architecture Tour from Magnificent MileChicago River 90-Minute Architecture TourChicago: Museum of Ice Cream Entry TicketChicago Loop District Food Tour with Deep Dish & Beef SandwichChicago Favorites Ultimate Food and Walking Tour iFLY Chicago Lincoln Park: First Time Flyer ExperienceChicago: Field Museum of Natural History Ticket or VIP TourChicago: Highlights & Attractions Walking TourChicago: 2-Hour Kayak Rental from BridgeportChicago: Moonlight Paddle Tour on the Chicago RiverChicago: Medieval Torture Museum Ticket with Ghost HuntingChicago: 45 Minute Architectural Sightseeing CruiseChicago: Classic Food & Walking Tour with Free Bike or KayakChicago: Architecture River Cruise from Michigan Avenue
Chicago Yacht CharterChicago Travel EssentialsChicago SurfingChicago Connectivity SolutionsChicago Walking ToursChicago Group ToursFood & Drink in ChicagoChicago Boat TicketsChicago Local Tour GuidesBoat Experiences in ChicagoChicago Sports & AdventureWater Activities in ChicagoChicago Day ToursChicago City PassChicago ActivitiesTawau Division ClassesSapa JR PassHa Long Cultural ExperienceNha Trang DivingPhu Quoc Island ClassesTottori Prefecture JR PassHakone ClassesHakone JR PassMiyazu Costume ExperienceSeville Cultural ExperienceKunming Yunnan Ethnic Village Half Day Private Tour Lunar New Year availability for RealNZ Milford Sound / Piopiotahi 1-day tour cruise · Round-trip from Queenstown to Te AnauPrivate Dongchuan Red Land Adventure from Kunming – Witness Nature's MasterpieceAppenzell Day Tour in Switzerland|Chocolate factory and cheese workshop tour with tasting1-day tour to Rhine Falls and Appenzell in Switzerland|Chocolate factory and cheese workshop tour with tastingMunich private charter day tour: Olympiapark München + BMW Museum + New Town HallFrom Tbilisi Kakheti Region Signaghi Bodbe Group Guided TourHalong Bay Luxury Cruise With Buffet Lunch Full-day Tour From HanoiNanjing Day Tour/Guide/Chinese/English/Russian Itinerary Adjustable 4-Hour Guide ServiceBatu Caves & Genting Highlands Day Tour – A Journey of Wonders & Hidden EscapesThings to do in JilinThings to do in SeogwipoThings to do in AtlantaThings to do in SapaThings to do in Hoa Lu DistrictThings to do in Palma de MallorcaThings to do in GoremeThings to do in HurghadaThings to do in GuangzhouThings to do in JohorThings to do in GuilinThings to do in IndonesiaThings to do in DalatThings to do in Da NangThings to do in ChinaReviews/Trip Moments
★
★
★
★
★
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.★
★
★
★
★
Reviews: Chicago: Ultimate City Attractions Bike Tour
Guest User2025-09-15
Amazing guide and tour. Bikes were excellent and gave us chance to see so much of the city you wouldn’t access on any other tour. Loved it!!★
★
★
★
★
Reviews: Chicago in a Day: Food, History & Architecture Walking Tour
Guest User2025-11-20
Exciting and entertaining right to the end. Rich has a lot to say and answered all questions. This tour of Chicago's culinary highlights is 100% recommended for every European!★
★
★
★
★
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!★
★
★
★
★
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!
About
Payment methods
Our partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.
Site Operator: Trip.com Travel Singapore Pte. Ltd.