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Free Chicago Walking Tours

4.9 (36 reviews)
Closed 9:00 am - 5:00 pm

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7 years ago

I've seen Chicago with new eyes. Thanks Paul! I will no longer take the awesomeness of my city for granted- I've seen it with new eyes. Wow!

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6 years ago

Great tour! Details of the places you couldn't find elsewhere. Good pace. Guide was fun, courteous and friendly. Highly recommend this

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Ask the Community - Free Chicago Walking Tours

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Review Highlights - Free Chicago Walking Tours

Matt was extremely knowledgeable and very patient with my young son who had many questions.

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Chicago Detours - Beyond dates and names of architects, we dig into the ways in which we interact with architecture.

Chicago Detours

4.9(273 reviews)
3.3 miRiver West, Noble Square, West Town

During Parents' Weekend at the University of Chicago, the university offered tours of the…read moreneighborhood through Chicago Detours. My wife did this tour a couple years ago and highly recommended it, but I wasn't especially interested because I had also gone to school here and figured I knew enough about Hyde Park already. However, she insisted that it would be worth our while and so I agreed to climb on the bus. And it was the absolutely right decision, because the tour was excellent. In fact, it wasn't just a tour of Hyde Park. It included the surrounding neighborhoods of Washington Park, Kenwood, Jackson Park, and Woodlawn. Since this was a UChicago sponsored event much of the information related to the University's investment and involvement in the area. Our tour guide and founder of Chicago Detours, Amanda, is herself a graduate of UChicago and thus she had some additional insight into the relationship with the community. Though the 75-minute tour felt a little slow-going at times, there was much to learn about the vibrant but sometimes troubled history of the area. Amanda has tremendous knowledge and the excursion was both fascinating and entertaining. I can imagine that Chicago Detours would have equally interesting tours of other neighborhoods in this diverse city.

Virtual tours are such a cool thing to do right now. I attended a Yelp Elite event that was a…read morevirtual food tour of Chicago. It was incredibly informative and a good balance of history and current trends. Looking forward to attending more virtual tours, like the World's Fair and the Cruise From Your Couch Boat Tour. I loved seeing the pictures of the in-person tours and can't wait to attend some of those too.

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Chicago Detours - On an architecture tour, you'll venture into spaces many locals don't know

On an architecture tour, you'll venture into spaces many locals don't know

Chicago Detours - Enjoy drinks in opulent settings like the Chicago Athletic Association Hotel on the 1893 World's Fair Walking Tour with Bars and Food.

Enjoy drinks in opulent settings like the Chicago Athletic Association Hotel on the 1893 World's Fair Walking Tour with Bars and Food.

Chicago Detours - Historic Walking Tour with Bars- drink, learn, eat, explore.

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Historic Walking Tour with Bars- drink, learn, eat, explore.

Inside Chicago Walking Tours

Inside Chicago Walking Tours

5.0(111 reviews)
1.8 miThe Loop

Colleen was great during our Chicago interior architecture tour. We went to six different buildings…read moreand she had super interesting points to share during each stop. She was thoughtful in offering restroom breaks during the two hour tour. Would absolutely recommend this tour - I have been to Chicago multiple times and learned more on this tour than I ever did in my previous visits combined. Fun way to see the city and stay (mostly) warm since it's a tour of the interior of buildings :)

I have taken many tours in different cities at home and abroad. Chicago being the birthplace of the…read moremodern skyscraper has many stories to tell about the evolution of turn of the century architecture after the great Chicago fire. Locally we have a great city guide on our local PBS channel 11 who does a fantastic job at uncovering some of the best forgotten stories about our cities past. Of course, I am referring to Geoffrey Baer, whom I have watched on our local PBS many times over the years. So yes, I can say that I am a fan. But you know it's one thing to watch these architectural marvels on TV or in person. I decided to be a tourist in my own city by taking the Original Chicago Architecture Interiors Tour by Inside Chicago Walking Tours. How was it? I loved it. Many of the treasures we uncovered, I have walked by for many years without every going inside and seeing the marvelous interiors firsthand. We also went over the exterior of several buildings that I never stopped to think about the stories behind the buildings history. Yes, I took a lot of buildings for granted. On this tour we went over the timeline and historical evolution of some of some of the significant buildings in our downtown area. Of course, were not able to cover all of them because Chicago is blessed to have so many great buildings with a storied past. I highly, highly recommend this tour to tourists and locals alike. Some of the buildings that were covered were the Chicago Board of Trade, The Federal Building, The Marquette, The Palmer House, and the Chicago Cultural Center (and many more). If you decide to take this tour get ready to be wowed and enlightened about Chicago.

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Inside Chicago Walking Tours
Inside Chicago Walking Tours
Inside Chicago Walking Tours

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Free Chicago Walking Tours - walkingtours - Updated June 2026

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