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Chicago Detours

Chicago, IL 60604
+1 312-350-1131
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Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour
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Historic Chicago Walking Bar Tour
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3-Hour Walking Tour: Chicago World's Fair of 1893
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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.
  • Excellent90%
  • Very good7%
  • Average1%
  • Poor1%
  • Terrible1%
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Open Now
All hours
Hours Today: 12:00 AM - 5:00 PM, 10:00 PM - 12:00 AM
Suggested Duration: 1-2 hours
Chicago, IL 60604
Downtown / The Loop
+1 312-350-1131
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Reviews (395)
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1 - 10 of 391 reviews

Reviewed 5 days ago


Thank lyonness57
Reviewed 1 week ago


Thank Travis C
Reviewed 1 week ago via mobile

I took the Wicker Park walking tour. Our guide, Elizabeth, was very knowledgable and entertaining. She took us to great spots and told us everything about the history of the neighborhood. The food spots were fantastic and I can't wait to go back and get...More

Thank Chase W
Reviewed 1 week ago via mobile

I really loved the Interior Architecture Walking Tour. We went to places I would not have seen without the tour. Amanda was wonderful and had really done her research. She kept everything interesting. The tour took 2 hours but we didn’t walk too far as...More

Thank MargotU761
Reviewed 3 weeks ago via mobile

So much fun! Our guide Elizabeth was knowledgeable and entertaining. This tour was a mix of Chicago history, silly games, drinks, and architectural history. I highly recommend you spend 3 hours on this tour.

Thank JanMaino
Reviewed 4 weeks ago

Found Alex to be a great guide with a lot of knowledge base and fun facts. I enjoyed the areas we visited and really like he had us be active in the discussion of the buildings or area. Would have liked more in the pedway...More

Thank CBLB503
Reviewed 18 September 2017 via mobile

We took the interior architecture walking tour with Amanda, who had the most interesting facts about places in Chicago that you wouldn't imagine. It is outstanding the amount of precious details the city has to offer, and sometimes people just walk by, this is a...More

Thank ConnieMartz
Reviewed 18 September 2017

Sonny took us on the tour a week ago..the group was small and the tour was interactive amongst the group which was so different - rather than just being lectured too. She took us to some amazing places which made the rest of our stay...More

Thank plum176
Reviewed 18 September 2017 via mobile

This was a walking tour, but that's loosely used. The tour itself went in and around the downtown "Loop" of Chicago and stopped at interesting and historically relevant places. We were really into the places most tourist don't get to see. The format is walk...More

Thank Joseph C
Downtown / The Loop
Often visitors' first stop in Chicago, The Loop is a
good starting point to sample the city's energy and
flavor. This central business district boasts
Michelin-rated restaurants, upscale hotels, premier
shopping, and enough arresting architecture to keep
your camera busy for hours. You won’t find too many
photo galleries of downtown Chicago without a shot of
Millennium Park and Cloud Gate (“The Bean”), one of
Sponsored by:
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