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Inside Chicago Walking Tours

5.0 (115 reviews)
Closed • 9:00 am - 6:00 pm

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William G.

I have taken many tours in different cities at home and abroad. Chicago being the birthplace of the modern 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.

The Rookery
kris r.

We had a wonderful and informative tour given by Adam. We are both Chicagoans and learnt a lot about Chicago architectural and general history. So much interesting information. Looking forward to going on another tour from this group.

Henry was an amazing guide. He brought his passion for architecture and engineering to our Art Deco tour, showing us the optimism and opulence of the era. I can't recommend this tour enough.

Ease of booking Pleasant customer service Tour guide Kaylee excellent Extremely knowledgeable and interesting

Kylie, as a tour guide, is animated but loud and clear in her delivery.
Ron O.

As the tour guide, Kylie was very knowledgeable and, most importantly, a great and pleasing personality that made the tour educational and pleasant despite the biting cold! (We're from California!) Also, we were running late because of the Chicago BOA Marathon, but Hillary from the tour office ensured we did not miss our tour. She and Kylie coordinated so we could still join the tour despite being 20 minutes behind.

Tiffany Ceiling

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9 years ago

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12 years ago

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7 years ago

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10 years ago

I have taken two tours with Hillary. Fabulous and educational experience. Highly recommended.

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11 years ago

We thoroughly enjoyed our walking tour. Hillary was a fantastic guide and gives you the facts! not the fiction. Definitely would recommend.

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11 years ago

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12 years ago

Personalized tour - fun and informative!! Thanks for the inside info on Chicago.

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Page 3 of 3

Ask the Community - Inside Chicago Walking Tours

Review Highlights - Inside Chicago Walking Tours

“Five friends came with me today on a private 2-hr tour of a slice of Chicago with Hillary from Inside Chicago.”

Mentioned in 48 reviews

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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.

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Inside Chicago Walking Tours - architecturaltours - Updated November 2026

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