We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
The latest reviews. The lowest prices. The perfect place to shop for hotels.
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Get directions
Address: Chicago, IL 60604
Phone Number:
+1 312-350-1131
00:00 - 21:00
22:00 - 00:00
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.

read more
Book In Advance
More Info
and up
Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour
More Info
and up
Historic Chicago Walking Bar Tour
More Info
and up
Walking and Food Tour: Chicago World's Fair of 1893

TripAdvisor Reviewer Highlights

Read all 351 reviews
Visitor rating
  • 310
  • 28
    Very good
  • 5
  • 2
  • 2
Great interior architectural tour

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... read more

Reviewed 4 days ago
Add Photo Write a Review

351 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
  • More
Showing 347: English reviews
Level Contributor
97 reviews
45 attraction reviews
common_n_attraction_reviews_1bd8 28 helpful votes
Reviewed 4 days ago NEW

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
Blacklick, Ohio, USA
Level Contributor
20 reviews
6 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
Reviewed 1 week ago

We visited Chicago in April and scheduled the architectural walking tour. Our guide, Eric, was informative and entertaining. We were shown several locations in a half-mile walk that included buildings famous and not so famous. I would recommend this two-hour tour for adults and families of all ages!

Thank Lynn-JohnC
Level Contributor
171 reviews
41 attraction reviews
common_n_attraction_reviews_1bd8 35 helpful votes
Reviewed 1 week ago

We went on the Chicago World's Fair Walking Food Tour in January. At the time it was advertised as a walking food tour with one glass of wine or beer and food samples for a light meal. When the tour guide arrived, she collected money from us for our beer or wine. We questioned this and she said they changed... More 

Thank CKay711
Pittsburgh, Pennsylvania
Level Contributor
43 reviews
21 attraction reviews
common_n_attraction_reviews_1bd8 18 helpful votes
Reviewed 1 week ago

Alex was a very enthusiastic tour guide, he had lots of great stories about architecture and the city of Chicago. Did the Pedway tour, that lasted about 2 hours, some of it is inside, some outside, not a long or difficult walk. I would encourage anyone to take this informative walking tour.

Thank summerfish1971
2 reviews
Reviewed 2 weeks ago

I used to live in Chicago and I still learned tons of stuff on the interior architecture tour I took. Our tour guide, Alex, was enthusiastic, knowledgable, and helpful and was full of great little insights to the spots he took us. I'm going to try to get my company to book a group tour this summer.

Thank Meryl W
Level Contributor
65 reviews
15 attraction reviews
common_n_attraction_reviews_1bd8 22 helpful votes
Reviewed 2 weeks ago via mobile

We've lived in the Chicago area all our lives but were interested in seeing some less visited sites. The interior architecture/pedestrian tour delivered. Alex was knowledgeable and well versed in the city's history. Also, we had to change the dates from the tour we originally booked and all it took was a quick call. Looking to take another tour with... More 

Thank aanniea
Kensington, Maryland
2 reviews
Reviewed 2 weeks ago

The lady escorting us, Elizabeth, has a masters. She was so knowledgeable on Chicago history and funny and sweet to boot. Great casual way to see Chicago.

Thank Theresa r
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 2 weeks ago

I have done this tour twice and with two different groups of people (my parents and my friends from out of town), and both times, it has been a huge success. If you like architecture, history, stories, great tour guides, and good food and beer, then this is the tour for you. You move quickly through a very interesting part... More 

1 Thank Kevin A
Bartlett, Illinois
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
Reviewed 2 weeks ago

Wonderful tour for locals & out-of-town visitors. Elizabeth was most informative and kept the tour moving along with just the right amount of information and fun facts. I would recommend this tour to broaden your Chicago knowledge & hear stories about the iconic buildings and statues that make our city so interesting!

Thank LCB832
Indianapolis, Indiana
Level Contributor
28 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 3 weeks ago via mobile

My boyfriend and I visited Chicago for the weekend. Based on reviews, we booked the Historic Chicago Walking Bar Tour for Saturday evening. We met the tour guide 10 minutes prior to start time of 5:45 PM. There were eight total purchase books in the tour… We were from the Midwest, Canada, Michigan, United Kingdom, Australia and Poland. Our tour... More 

Thank Trekster1

Travellers who viewed Chicago Detours also viewed


Been to Chicago Detours? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Chicago Detours and other visitors
1 question
Ask a question
Questions? Get answers from Chicago Detours staff and past visitors.
Posting guidelines
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?