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Top Picks for Chicago Day tours

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

Trip.com offers 120 Day tours in Chicago

Q: What are the best Day tours in Chicago?

1-day tour of Chicago, USA Chicago by Night River and Lake Cruise City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise

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Discover 120 Day tours in Chicago on Trip.com, updated October 16, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From NZD 17.45 per person, with an average total of NZD 108.95. Choose the option that suits your plan.

With 8.63k 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 4.344k reviews and a 4.7 rating.

Now on Trip.com: "1-day tour of Chicago, USA", a 5-hour adventure in Chicago!

The next available day tour departs on October 17, 2025. Book now to secure your spot!

Chicago Day tours usually take about 5 hours — perfect for a relaxed, immersive experience!

53% of Chicago Day tours now offer English-speaking guides

October 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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120 Results for Chicago Day tours

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1-day tour of Chicago, USA
󱩳[Wind City Tour] See the magnificent scenery of Chicago, visit classic landmarks, and feel the charm of "post-modern architectural style";
Duration: 5.7 hrs
English
4.5/5
Satisfactory· 4 reviews
FromNZD 262.17
Chicago by Night River and Lake Cruise
󱩳Cruise along the main branch of the Chicago River full of historic buildings
Duration: 1.5 hrs
4.7/5
Great· 14 reviews
FromNZD 78.56
City Cruises Chicago: Brunch, Lunch, or Dinner River Cruise
󱩳Creative cocktails, wine, and beer from our fully-stocked cash bar
Duration: 2–2.5 hrs
FromNZD 307.75
Chicago Loop: Art, Skyscrapers, Millennium Park & "The Bean"
󱩳Gaze at stunning works of art made from delicate, colorful Tiffany glass.
Duration: 2 hrs
5.0/5
Excellent· 6 reviews
FromNZD 85.81
Chicago: Treasures of the Golden Age Walking Tour
󱩳Hear about the city's architectural gems—museums, department stores, skyscrapers and concert halls—and the men and women who inspired them
Duration: 2 hrs
FromNZD 61.30
Chicago City Tour with Architecture River Cruise Option
Duration: 2–4 hrs
4.8/5
Great· 669 reviews
FromNZD 85.56
Chicago: Ultimate City Attractions Bike Tour
󱩳Behold the beautiful architecture of the Museum Campus
Duration: 3 hrs
5.0/5
Excellent· 8 reviews
FromNZD 104.72
Chicago: Prohibition-Era Culture & Architectural Treasures
󱩳End at Millennium Park and the iconic Bean
Duration: 2.5 hrs
5.0/5
Excellent· 1 review
FromNZD 85.53
Chicago: Shoreline Lake Michigan Skyline Cruise
󱩳Enjoy a fast entry process with a ticket that lets you skip the ticket office
Duration: 45 mins
FromNZD 65.59
Chicago Favorites Ultimate Food and Walking Tour
Duration: 3 hrs
4.9/5
Excellent· 1.8k reviews
FromNZD 148.55
Chicago City Minibus Tour
Duration: 2 hrs
4.9/5
Excellent· 324 reviews
FromNZD 83.81
Chicago: Magnificent Mile Tour With Optional 360 Chicago
󱩳Admire Art Deco, Beaux-Arts, and neoclassical architecture.
Duration: 2–3 hrs
5.0/5
Excellent· 2 reviews
FromNZD 68.31
Chicago: Shoreline All Day Water Taxi
󱩳Enjoy a fun and fast way to get around Chicago with a water taxi day pass
5.0/5
Excellent· 1 review
FromNZD 62.72
Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus
󱩳Hear the stories that made Chicago through engaging digital commentary
Spanish
4.0/5
Good· 4 reviews
FromNZD 78.56
Chicago River 90-Minute Architecture Tour
Duration: 90 mins
4.7/5
Great· 4.3k reviews· 133 booked
FromNZD 78.58
Chicago: Creepy Cruise
English
FromNZD 73.27
Chicago River 45-Minute Architecture Tour from Magnificent Mile
Duration: 45 mins
4.7/5
Great· 1.4k reviews· 169 booked
FromNZD 48.90
Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929
Duration: 1 hr
English
FromNZD 87.01
Chicago lakefront neighbourhood bike tour
󱩳Enjoy one of the most popular bike tours Chicago has to offer
English
FromNZD 17.45
Chicago Bus Tour: 90-Min Sunset Tour
Duration: 90 mins
English
FromNZD 77.40
Ultimate city bike tour in Chicago
󱩳Spot all of Chicago's top sights on a guided bike tour
English
FromNZD 19.20
Signature dishes of Chicago bike tour
󱩳Ride around Chicago as you listen to an expert guide
English
FromNZD 157.14
Chicago Pizza Bus Tour Ticket
Duration: 210 mins
English
FromNZD 139.74
Chicago Downtown: 3-Hr Guided Pizza Tour
Duration: 3 hrs
English
FromNZD 108.34
Hidden In Plain Sight: Chicago Prohibition Tour
Duration: 210 mins
English
FromNZD 70.65
Scenic Chicago Night Tour
Duration: 210 mins
English
FromNZD 294.82
Original Chicago Prohibition Tour
Duration: 4 hrs
English
FromNZD 95.95
Chicago: Guided Highlights Tour + SkyDeck + Architecture Cruise
Duration: 4 hrs
English
FromNZD 225.04
Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters
Duration: 2 hrs
English
FromNZD 85.49
Chicago: Craft Brewery Barrel Bus Tour
Duration: 225 mins
English
FromNZD 156.38
Chicago: Highlights & Attractions Walking Tour
Duration: 2 hrs
English
FromNZD 86.53
Chicago: Culture & Architecture Guided Tour
Duration: 150 mins
English
FromNZD 85.49

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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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Reviews/Trip Moments

★

Reviews: 1-day tour of Chicago, USA

Guest User2024-07-02

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

★

Reviews: Chicago by Night River and Lake Cruise

Guest User2025-08-07

You board a boat. You navigate the river to the gates to cross into Lake Michigan. It's a great experience, as you have to wait for the water level to rise or fall before the boat can travel to or from Lake Michigan. The view at night is incredible. Bring mosquito repellent because there are mosquitoes at night. Highly recommended.

★

Reviews: Chicago Loop: Art, Skyscrapers, Millennium Park & "The Bean"

Guest User2025-04-05

This tour of the Chicago Loop was excellent. The guide was friendly and knowledgeable, sharing fun and fascinating facts about the city. I learned so much and enjoyed every minute.

★

Reviews: Chicago City Tour with Architecture River Cruise Option

Guest User2025-07-29

Avery was an excellent guide! He was very knowledgeable and we learned a lot from the tour. We loved having a few moments to get out, stretch, and get a closer view of some of the historical buildings. Everyone should ask for Avery! He gets five stars from all of our family members.

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