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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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Closed 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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141 - 150 of 384 reviews

Reviewed April 19, 2016 via mobile

Had a great time on the Historic Chicago Walking Bar Tour back in March. Pawel was awesome! He answered all my random questions and gave us some really helpful advice on what to do after the tour. Looping forward to joining Chicago Detours on their...More

Thank Sylwia B
Reviewed April 18, 2016

We were in Chicago for a regional conference and the group went on the Jazz/Blues tour as a networking activity. Amanda, our tour guide, was amazing! The bus was very nice! We learned a lot about areas of Chicago many of would probably never get...More

Thank aliciabingham2016
Reviewed April 13, 2016

We took the "Pub Crawl" historical tour. It's not a Pub Crawl at all. It is a great historical architecture tour with stops for beer or wine and appetizers, which is why I only gave it a very good rating. Our tour guide Elizabeth was...More

Reviewed April 12, 2016

Nice mixed use of Ipad for historical context and verbal info from the guide. Saw some of the detail inside the buildings I would have missed otherwise.

Thank Kathy C
Reviewed April 5, 2016

It was different than I expected. Thought it would be purely a focus on the pedway, but it was so much more. In retrospect, I would have been bored with simply a pedway tour. They did this right.

Thank bsvo742421
Reviewed March 25, 2016 via mobile

I took the Loop Interior Architecture Walking Tour with Pedway tour and was well pleased. The tour was very informative and the guide, Elizabeth, was very knowledgeable (it seemed to help that she was a Chicago native, gave it more of a personal touch) and...More

Thank Emma S
Reviewed March 25, 2016

Very unique tour of Chicago. Even as a native I still learned a lot from the tour and saw places in Chicago I never been to before.

Thank Ricardo S
Reviewed March 19, 2016

My two friends and I were in town to visit a friend and were looking for interesting ways to see the city. I stumbled upon Chicago Detours on google and decided to give it a shot. We had a phenomenal time! We did the Historic...More

Thank Jillian D
Reviewed March 17, 2016

I wanted to do a tour with the Chicago Architectural Society. But for the day we would be in Chicago, all they had was a Frank Lloyd Wright suburb tour -- I'm sure that would have been nice, but we wanted something in the city....More

Thank kathy884
Reviewed March 1, 2016

In January I went on the Loop Interior Architecture Walking Tour with Pedway. I was really surprised by all of the knowledge our guide shared with us. This is not something that one could easily look up online. We even got a our own copy...More

Thank Johanna W
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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