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Address: Chicago, IL 60604
Phone Number:
+1 312-350-1131
22:00 - 00:00
00:00 - 17:00
Open now
See all hours
Sun 00:00 - 21:00
Sun - Sat 22:00 - 00:00
Mon - Sat 00:00 - 17:00
Recommended length of visit: 1-2 hours

This is not your grandma's architecture tour! Our award-winning guided...

This is not your grandma's architecture tour! Our award-winning guided tours of Chicago’s architecture, history, and culture bring curious people to explore stories and places locals don't even know. With Chicago Detours, you'll explore downtown and our diverse neighborhoods to experience the city’s interior architecture, the underground Pedway, jazz and blues, and

historic bars.


Founded by a former Rick Steves tour guide, Chicago Detours has designed tours that are fun, educational experiences. Our tour guides are are not just volunteer docents, they’re highly trained and educated professionals who know how to spark discussions and create a lively group dynamic. Rated five stars on both Yelp and TripAdvisor, Chicago Detours is one of the top-rated tour companies in the city. We offer regularly scheduled tours for the public, and private group tours for corporate team-building, student field trips, and convention groups.


The public walking tours stay mostly indoors, making them great activities for any time of year. Options include the "Loop Interior Architecture Walking Tour," which explores beautiful building interiors and the underground Pedway System, and the "Historic Chicago Walking Bar Tour," which digs into Chicago's entertainment history of social clubs, jazz music, prohibition, and theater. Other public tours include the "Best Architecture Walking Tour Since Sliced Bread," "1893 World's Fair Walking Tour with Bars," and "Pilsen Spaces and Changes Walking Tour with Food."


Private group tours include the outings mentioned above, as well as tours by a luxury coach equipped with screens for presentation of historic images and videos. Many of our private group tour options can operate in the evening, and can include food and drink. Our historic bar tours, both by foot and by bus, are the most popular with private groups. Your group will eat, drink and learn about how Chicago has had fun over its history. The "Big Shoulders Historic Bar and Food Bus Tour" visits Bridgeport, Chicago's oldest neighborhood outside downtown, which was home to workers for the nearby Union Stock Yards.

Another popular tour is our "Jazz, Blues & Beyond by Bus." This tour explores Chicago neighborhoods north to south for a fun, up-close connection with the cultural history of Chicago's music. This memorable experience reaches its conclusion when a blues musician comes on board for a performance and harmonica lesson.

Other private tours include "Chicago Neighborhoods and Cultural Diversity by Bus" and "Old Polonia and Wicker Park Tour with Food." Step-on guide services are also available for private group tours. Tours include lively guide commentary, an interactive group dynamic, and extras like media presentation and special gifts. Rather than a standard lecture format, these tours actively involve guests in a memorable experience that inspires new perspectives of the city's architecture and history.

We annually receive TripAdvisor's "Certificate of Excellence," and maintain five stars on Yelp as well. Our tours have been featured in Frommer's, Lonely Planet, ABC 7, WGN, WBEZ, "Chicago Magazine," the Chicago Tribune, and the Guardian.

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Book In Advance
More Info
USD 26.00*
and up
Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour
More Info
USD 38.00*
and up
Historic Chicago Walking Bar Tour
More Info
USD 66.00*
and up
Old Polonia and Wicker Park History and Food Tour

TripAdvisor Reviewer Highlights

Read all 359 reviews
Visitor rating
  • 318
  • 28
    Very good
  • 5
  • 2
  • 2
Fabulous Chicago architecture tour

Paul was a fabulous guide for our tour. He was very enthusiastic in sharing his knowledge about architectural highlights in Chicago. We learnt so much. A must do tour when in... read more

Reviewed 1 week ago
Melbourne, Australia
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359 Reviews from our TripAdvisor Community

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Showing 355: English reviews
Melbourne, Australia
Level Contributor
5 reviews
3 attraction reviews
Reviewed 1 week ago

Paul was a fabulous guide for our tour. He was very enthusiastic in sharing his knowledge about architectural highlights in Chicago. We learnt so much. A must do tour when in Chicago.

Thank Cantwait09
1 review
Reviewed 1 week ago

The tour was really great! Even though I'm a local, I learned so many things, you'll never look at the Loop the same again. The guide was awesome, very interactive, with videos and old pictures.They even send you more information for later. I definitely want to try the rest of the tours!

Thank Susan M
Sacramento, CA
Level Contributor
35 reviews
19 attraction reviews
common_n_attraction_reviews_1bd8 96 helpful votes
Reviewed 2 weeks ago

Having already taken the boat tour in the past, I decided to try something different. The Chicago Detours group works hard to research the history and culture of Chicago and then ties it in to the interior architectural features of the buildings that are visited. The 2 hour tour just flew by - it felt like only 30 min as... More 

Thank 61luv2travel
Ellsworth, Maine
1 review
Reviewed 2 weeks ago

Being from Maine, my friend and I a wonderful time learning about Chicago through this tour! Our guide was fantastic, knowledgable and so much fun! I would book another tour with this company the next time I visit! Thank you!

Thank jmyers007
Homer Glen, Illinois
Level Contributor
4 reviews
Reviewed 3 weeks ago

We had a wonderful tour with Alex yesterday on the Interior Architectural Walking Tour. I highly recommend this tour as I learned many things I never new as a Chicago native. A visitor to Chicago would really appreciate it. Alex is extremely good giving a lot of information along with keeping everyone going so we finished exactly on time. I... More 

Thank mhiggins354
1 review
Reviewed 3 weeks ago

Alex was our tour guide for the Loop Interior Architectural tour and being from Chicago, I expect to know a decent amount, but I was pleasantly surprised to learn a great deal more about my city! He kept it very entertaining and I learned so much about some of the city buildings and history that I had no idea about!... More 

Thank Andy P
Ypsilanti, Michigan
2 reviews
Reviewed 4 weeks ago

This sounded like a fun tour and it exceeded my expectations. Our guide, Amanda, was dynamic, highly knowledgeable and really kept us engaged throughout. The buildings featured were fascinating and the insights provided a terrific tapestry of cultural and historic context. The drinks and appetizers certainly added to the awesome experience. Along the way there were even fun little quizzes,... More 

Thank whoisdonald
1 review
Reviewed 4 weeks ago

My husband and I really enjoyed the Historic Chicago Walking Bar Tour! Our tour guide Pawel was friendly, fun, and very knowledgeable -- with interesting facts and funny stories about Chicago's architectural and cultural past. We paid for our drinks up front, and they were waiting for us when we arrived at each stop! There were also fun little appetizers... More 

Thank Kathy P
Dubuque, Iowa
Level Contributor
4 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 4 weeks ago

Elizabeth was our guide and she was highly knowledgeable about Chicago history, architecture, and social customs. And entertaining too. The use of iPads to share video and historical photos enhanced the tour. I've been visiting Chicago for 30 years, and it was time to learn more about this city than my usual tourist stops. So glad that I went.

Thank mark n
Level Contributor
100 reviews
46 attraction reviews
common_n_attraction_reviews_1bd8 30 helpful votes
Reviewed 20 April 2017

Chicago has great architecture and history to explore inside the beautiful buildings and outside along the river and streets. Chicago Detours offers a 2 hour walking tour within, around, and underneath central city locations. Elizabeth, our guide, was providing great insight and history throughout the tour. Places you never have appreciated are highlighted and explained. Enjoy the adventure of learning... More 

Thank MB M

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?