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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 and Food 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: 00:00 - 17:00, 22:00 - 00:00
Suggested Duration: 1-2 hours
Chicago, IL 60604
+1 312-350-1131
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Reviews (380)
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1 - 10 of 376 reviews

Reviewed 5 days ago

REALLY enjoyed this tour. Pavel was so informative...entertaining...courteous...and proud of Chicago. He handled our group with compassion and patience. A couple of people were late and one in particular was unpleasant but he was gracious. His enthusiasm was contagious

Thank Sarah B
Reviewed 1 week ago

Tour guide Alex was great, very enthusiastic and knowledgeable. You get to see the places you would just walk by in a different light and you suddenly realize how much history is hidden in Chicago. The beers and snacks were really good - a great...More

Thank d0nsch0
Reviewed 1 week ago

This tour is a great intro to Chicago's history and architecture, and if you didn't think you were interested in either of those things before, you will be. 2 hours isn't long enough, and you'll want to see and know more when you're finished. Alex...More

Thank erinlionbear
Reviewed 1 week ago

We spent a very enjoyable day following Alex around the Loop, first for the Loop Interior Architecture Tour and then for the 1893 World’s Fair Tour. He is personable, knowledgeable and witty. He uses images on an I-pad and games like scavenger hunts to engage...More

Thank ratherBtravelling_11
Reviewed 1 week ago

I took a walking tour "Architecture for Design Lovers" in the loop. Even though I've been a Chicago resident for over 40 years, this 90-minute, 3-block walk gave me new insights into the evolution of historical design, function and “personalities” of buildings I’ve walked past...More

Thank cheryls741
Reviewed 2 weeks ago

Alex was a great guide to many places I'd walked past but never really looked at. I learned about the renewal efforts downtown, some common myths about Chicago were debunked, and the pedway system was a revelation! We had plenty of time to look, take...More

Thank travelg38
Reviewed 2 weeks ago

I've lived in Chicago for a little under a year and wish I had gone these tours sooner. I went on the Bar Tour with Elizabeth after I had already taken the Interior Architecture Tour with Pawel. Both tours are in the Loop, which is...More

Thank Morgan L
Reviewed 3 weeks ago via mobile

We chose the Pedway tour which took us to a part of Chicago that we knew nothing about. We were not disappointed. Elisabeth- a Lead Tour Guide - was so full of information about the city and its origins and growth with observations that we...More

Thank JOE1949B
Reviewed 4 weeks ago

If you haven't craned your neck to look way up at the ceiling inside Macy's (the old Marshall Fields) or gone inside the Chicago Cultural Center, you've missed Chicago's Tiffany ceilings. The ceilings were our "find" from Chicago Detours' Loop Interior Architecture walking tour. Alex,...More

Thank Hallie K
Reviewed 5 weeks ago

The Historical Chicago walking bar tour was fun. Elizabeth didn't stop talking the entire time with history and tid-bits of info. Not sure how she can memorize all that! But eat before you go. Don't count on the "appetizers". After the tour, our group headed...More

Thank cschneider6660
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