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Top Chicago Day Tours

Q: How many Day tours are available in Chicago on Trip.com?

Trip.com offers 111 Day tours in Chicago

Q: What are the best Day tours in Chicago?

Chicago Downtown + Millennium Park Day Tour in the US Chicago: City Minibus Tour with Optional Architecture Cruise Small Group Max 12: Chicago Architecture and Aesthetics Tour

Q: How can I contact Trip.com customer support?

Get help anytime, anywhere within 30 seconds Contact customer support

Q: Can I change or cancel my booking?

Change and cancellation policies vary by attractions and tours. Please check the product details page for more information.

Q: How can I get discounted prices?

Ticket prices may vary between weekdays and weekends, as well as during peak and off-peak seasons. When booking with Trip.com, you can also use Trip Coins to get extra savings. For more tips on booking discounted tickets, please visit Trip.com for the latest information.

Discover 111 Day tours in Chicago on Trip.com, updated February 5, 2026, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From JPY 4,395.00 per person, with an average total of JPY 9,245.33. Choose the option that suits your plan.

With 13.944k 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 Downtown + Millennium Park Day Tour in the US", a 5-hour adventure in Chicago!

The next available day tour departs on February 6, 2026. Book now to secure your spot!

Chicago Day tours usually take about 5 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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111 results for Chicago Day tours

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Chicago Downtown + Millennium Park Day Tour in the US
Duration: 5.7 hrs
English
4.5/5
Satisfied· 4 reviews
FromJPY 23,499
Chicago: City Minibus Tour with Optional Architecture Cruise
Duration: 2–4 hrs
English
4.9/5
Excellent· 11 reviews
5% off
Limited-time sale
FromJPY 7,288JPY 7,672
Small Group Max 12: Chicago Architecture and Aesthetics Tour
Duration: 1.8 hrs
English
FromJPY 7,520
Chicago: Gangsters and Ghosts Guided Walking Tour
Duration: 2 hrs
English
4.9/5
Excellent· 250 reviews
5% off
Limited-time sale
FromJPY 5,487JPY 5,776
Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus
English
4.6/5
Satisfied· 91 reviews
5% off
Limited-time sale
FromJPY 6,700JPY 7,053
Lake Michigan Skyline Cruise in Chicago
Duration: 30–45 mins
English
4.5/5
Satisfied· 246 reviews
FromJPY 5,092
Chicago River 90-Minute Architecture Tour
Duration: 90 mins
English
4.7/5
Great· 4.3k reviews· 166 booked
FromJPY 7,063
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Duration: 45 mins
English
4.7/5
Great· 1.4k reviews· 193 booked
FromJPY 4,395
Chicago Crime and Mob Bus Tour
Duration: 90–120 mins
English
4.7/5
Great· 1.6k reviews
FromJPY 7,691
Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929
Duration: 1 hr
English
5.0/5
Excellent· 1 review
FromJPY 7,985
Chicago: Museum of Ice Cream Entry Ticket
Duration: 1.5 hrs
English
4.4/5
Good· 40 reviews
5% off
Limited-time sale
FromJPY 4,858JPY 5,114
Flyover in Chicago: An Immersive Flying Theatre Experience
Duration: 30 mins
English
4.9/5
Excellent· 96 reviews
5% off
Limited-time sale
FromJPY 5,683JPY 5,983
Chicago Favorites Ultimate Food and Walking Tour
Duration: 3 hrs
English
4.9/5
Excellent· 1.9k reviews
FromJPY 13,340
Lake Michigan Sunset Cruise in Chicago
Duration: 90 mins
English
4.6/5
Excellent· 433 reviews
FromJPY 7,063
Chicago Mobs and Haunts Walking Tour
Duration: 90–120 mins
English
FromJPY 5,337
The Art Institute of Chicago: Skip The Line Ticket + Exclusive Guided Tour
Duration: 150 mins
English
FromJPY 13,220
Chicago Lake and River Architecture Tour
Duration: 90 mins
English
4.6/5
Excellent· 1k reviews
FromJPY 7,063
Small-Group Tour of Chicago Neighborhoods: North and South Side
Duration: 270 mins
English
4.5/5
Excellent· 48 reviews
FromJPY 19,619
Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
Duration: 90 mins
English
4.8/5
Great· 569 reviews
FromJPY 5,624
Chicago: Mob and Crime Bus Tour
Duration: 1.5 hrs
English
4.7/5
Great· 50 reviews
5% off
Limited-time sale
FromJPY 7,324JPY 7,710
Original Chicago Architecture Interiors Tour: Dazzling Interiors
Duration: 2 hrs
English
4.9/5
Excellent· 1.5k reviews
FromJPY 5,494
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
English
4.9/5
Excellent· 313 reviews
FromJPY 13,655
Chicago: Taste of Chinatown Food and Cultural Walking Tour
Duration: 3 hrs
English
5.0/5
Excellent· 16 reviews
5% off
Limited-time sale
FromJPY 12,704JPY 13,373
City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise
Duration: 2–2.5 hrs
English
4.9/5
Excellent· 11 reviews
5% off
Limited-time sale
FromJPY 18,184JPY 19,142

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Frequently asked questions about Chicago Day tours

How many Day tours are available in Chicago on Trip.com?

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Trip.com Picks

Top Tours in Chicago

Best Experiences in Chicago

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Instituto de Arte de Chicago: Entrada sin colas + Visita guiada semiprivada Chicago: Crucero al atardecer con guía de 90 minutos Chicago: Visita sin colas al Instituto de Arte con guía Chicago: Guided Food Tasting + Bike Tour Chicago: Food and Prohibition Architecture Guided Tour Chicago: Crucero turístico arquitectónico de 45 minutos Chicago Night Crimes Bus Tour: Criminals, Mobsters and Gangsters Chicago: Recorrido guiado a pie por el barrio Loop Chicago round-trip|Dubuque Town + Galena Town + Grant Park Chicago: American Writers Museum Flexible Date Entry Ticket Chicago River 45-Minute Architecture Tour from Magnificent Mile Chicago: Underground Pedway & the Loop Guided Walking Tour Chicago: Tapas & Flamenco Dinner in Ukrainian Village Recorrido gastronómico y a pie definitivo por los lugares favoritos de Chicago iFLY Chicago Lincoln Park: First Time Flyer Experience

Wellness & Spa in Chicago Chicago Travel Essentials Chicago Day Tours Chicago Classes Chicago Local Tour Guides Chicago Spa & Massage Chicago Airport Services Food & Drink in Chicago Boat Experiences in Chicago Chicago Cultural Experience Chicago Travel Services Chicago Visa Application Services Chicago Transportation Chicago Shopping Discounts Bang Pa Travel Essentials Hokkaido Day Tours Sri Jayewardenepura Kotte Classes Boat Experiences in Osaka Taipei Day Tours Xi'an Transportation Fujikawaguchiko Visa Application Services Thailand City Pass Nagoya Sports & Adventure Xi'an Shopping Discounts Excursión de día completo en Rapa Nui Excursión de un día al Parque Nacional Hell's Gate y paseo opcional en barco por el lago Naivasha.Kumbhalgarh & Ranakpur Day Trip from Udaipur with Guide and Lunch 3 Hour shared Cinque Terre tour + Swim Stops at Secluded Beaches!Tzoumerka villages tour All in One Day Konorchek Canyon Issyk Kul Lake and Burana Tower Isla Tortuga, paraíso con snorkel incluido Excursión de un día a las cascadas de Materuni y a las aguas termales de Chemka Galveston Mansions and Murder Walking Tour MÁS VENDIDO: Excursión de lujo de un día en crucero por la bahía de Ha Long - Todo Incluido

Reviews/Trip Moments

★

Reviews: Chicago Downtown + Millennium Park Day Tour in the US

Guest User2024-07-02

The master is super nice, punctual and kind. The experience is great, overall it is great, the service is very good and the price is high.

★

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: Gangsters and Ghosts Guided Walking Tour

Guest User2026-01-22

Baylor was an excellent guide all around, knowledgeable and funny. This is a nice walking tour around the Loop downtown, takes about 1.5 hours. It was great to see the architecture and an added bonus that we were able to take inspiration of places to return to for drinks or shows.

★

Reviews: Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Guest User2025-11-10

Worked perfectly for us. Got a great overview of the city and learned a lot. Getting off and on was easy and buses ran as scheduled. All drivers and staff were helpful and friendly. Special shout out to Candance who went above and beyond expectations!

★

Reviews: Lake Michigan Skyline Cruise in Chicago

Guest User2024-09-13

Every seat on the boat brought exceptional views! The recorded tour guide gave wonderful information and facts about the scenery

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