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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 115 Day tours in Chicago

Q: What are the top-rated Day tours in Chicago?

Chicago: Secret Interiors Architecture Walking Tour Chicago's Original Dazzling Architectural Interiors Tour Chicago: City Minibus Tour with Optional Architecture Cruise

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Discover 115 Day tours in Chicago on Trip.com, updated September 28, 2025, with experiences lasting from 1 to 9 hours. Find the perfect adventure for your day!

From SGD 12.90 per person, with an average total of SGD 89.42. Choose the option that suits your plan.

With 2.962k verified reviews, Day tours Chicago boast an average rating of 4.8.

This week's most popular Day tours: "Original Chicago Architecture Interiors Tour: Dazzling Interiors", with 1.306k reviews and a 4.9 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 September 29, 2025. Book now to secure your spot!

Chicago Day tours usually take about 4 hours — perfect for a relaxed, immersive experience!

60% of Chicago Day tours now offer English-speaking guides

September is the perfect time to visit Chicago! Choose from Day tours available day tours, including seasonal favorites like Original Chicago Architecture Interiors Tour: Dazzling Interiors.

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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115 Results for Chicago Day tours

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Recommended

Chicago: City Minibus Tour with Optional Architecture Cruise

󱩳Create memories at 3 amazing photo stops, including one of the Chicago skyline

Duration: 2–4 hrs

4.9/5

Excellent· 14 reviews

FromSGD 63.23

Chicago: Architecture River Cruise Skip-the-Ticket Line

󱩳Cruise along all 3 branches of the Chicago River

Duration: 75 mins

FromSGD 61.80

Chicago City Minibus Tour

Duration: 2 hrs

4.9/5

Excellent· 309 reviews

FromSGD 61.92

Chicago: Secret Interiors Architecture Walking Tour

󱩳Discover the significance of various design elements and hidden features

Duration: 2 hrs

5.0/5

Excellent· 4 reviews

FromSGD 46.30

Chicago City Tour with Architecture River Cruise Option

Duration: 2–4 hrs

4.8/5

Great· 664 reviews

FromSGD 63.21

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Duration: 2 hrs

4.9/5

Excellent· 1.3k reviews

FromSGD 45.20

Lake Michigan Skyline Cruise in Chicago

Duration: 45 mins

4.5/5

Satisfactory· 246 reviews

FromSGD 41.97

Chicago's Original Dazzling Architectural Interiors Tour

󱩳Explore unknown beautiful spaces that even locals walk by every day

Duration: 2 hrs

5.0/5

Excellent· 4 reviews

FromSGD 45.22

Explore Chicago’s Hidden Past: Prohibition Culture & Architecture

Duration: 150 mins

4.8/5

Great· 90 reviews

FromSGD 64.52

Chicago Highlights Walking Tour with Skydeck & Cruise

󱩳Chicago Shoreline Cruise Admission (Included in Price)

Duration: 4 hrs

FromSGD 244.14

Chicago Walking Tour: Historic Treasures of Chicago

Duration: 2 hrs

4.9/5

Excellent· 321 reviews

FromSGD 45.20

Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929

Duration: 1 hr

English

FromSGD 64.35

Chicago lakefront neighbourhood bike tour

󱩳Enjoy one of the most popular bike tours Chicago has to offer

English

FromSGD 12.90

Ultimate city bike tour in Chicago

󱩳Spot all of Chicago's top sights on a guided bike tour

English

FromSGD 14.20

Signature dishes of Chicago bike tour

󱩳Ride around Chicago as you listen to an expert guide

English

FromSGD 116.20

Chicago Film and Television Tour: Skyscraper Fantasy Light and one-day tour

󱩳Today you will step into the prototype streets of Gotham City in "Batman: The Dark Knight" and feel the mystery and coldness under the Gothic architecture.

Duration: 3 hrs

English

FromSGD 162.13

Chicago Bus Tour: 90-Min Sunset Tour

Duration: 90 mins

English

FromSGD 63.69

Chicago Round-trip |Dubuque Town + Galena Town

󱩳Travel through Iowa's historic towns and enjoy the charming riverside scenery.

Duration: 9 hrs

English

FromSGD 133.43

Chicago: Creepy Cruise

English

FromSGD 54.26

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

FromSGD 193.69

Chicago: Craft Brewery Barrel Bus Tour

Duration: 225 mins

English

FromSGD 128.64

Hidden In Plain Sight: Chicago Prohibition Tour

Duration: 210 mins

English

FromSGD 58.13

Chicago Downtown: 3-Hr Guided Pizza Tour

Duration: 3 hrs

English

FromSGD 89.13

Original Chicago Prohibition Tour

Duration: 4 hrs

English

FromSGD 71.05

Scenic Chicago Night Tour

Duration: 210 mins

English

FromSGD 218.26

Chicago: Food and Prohibition Architecture Guided Tour

Duration: 5 hrs

English

FromSGD 127.88

Chicago: Chinatown Food & Culture Walking Tour

Duration: 3 hrs

English

FromSGD 103.34

Chicago: Guided Food Tour + Bike or Kayak Rental

Duration: 150 mins

English

FromSGD 109.79

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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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What are the top-rated Day tours in Chicago?

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Reviews/Trip Moments

★

Reviews: Chicago: City Minibus Tour with Optional Architecture Cruise

Guest User2025-09-01

Enjoyed touring many different areas and receiving lots of educational information on Chicago (with a great sense of humor, thanks to Rick).

★

Reviews: Chicago City Minibus Tour

Guest User2025-09-02

This was an amazing tour! Rick was an incredibly knowledgeable tour guide and provides you with great information while still keeping things light and making you laugh! He was never without an answer to a question either, and all while driving the tour bus! Photo ops were great, learning all of the history was great, highly recommended!!

★

Reviews: Chicago: Secret Interiors Architecture Walking Tour

Guest User2025-08-26

A very relaxed guide with a sense of humor and background knowledge. We thoroughly enjoyed the tour.

★

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.

★

Reviews: Original Chicago Architecture Interiors Tour: Dazzling Interiors

Guest User2025-09-15

The tour delivered as promised. Our guide was knowledgeable and interesting in how he delivered the context of the Chicago community and builders of the times. We covered five very different building interiors - two hours was packed! I would definitely recommend this tour company and specific tour! Great day being dazzled in the Second City.

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