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    Chicago Private Tours

    5.0 (28 reviews)
    Open 7:00 am - 11:00 pm

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    What a perfect way to explore Chicago!! My husband and I enjoyed a beautiful afternoon touring the city and local breweries. The tour was highly customizable, with excellent service, and super knowledgeable guides! We started the tour not knowing much about the city and ended the tour in love with CHI. Plan to return for our next trip! Thank you!!

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    Review Highlights - Chicago Private Tours

    Matt has such extensive knowledge and gives such a detailed history of the city you cannot help but fall in love.

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    Chicago Architecture Center

    Chicago Architecture Center

    (811 reviews)

    The Loop

    Chicago Walking Tour - Elevated Architecture Downtown 'L' Train…read moreWe have previously taken the CAC boat tour and one of the surface walking tours (both of which were great), but this time we wanted something with a slightly different perspective while staying downtown. We chose the Elevated Architecture Downtown 'L' Train tour led by Andrew, our CAC docent. As no one else had signed up for the tour that morning, it became a private tour. Andrew was not only very knowledgeable about the architecture and friendly, but also, given that he works in planning at the Chicago Metro, was able to take us on an even deeper dive concerning the "L", its history, and some of the current challenges. As we were about 35' about street level for the tour, we were also treated to a different perspective of the building and their design/decoration, something that cannot be readily observed from street level. Thans again to Andrew for an information and entertaining tour above the streets of downtown Chicago-truly a unique experience.

    If you're in Chiago you have to do the Architecture tour at least once. If you're in Chicago…read moreduring the Summer as I was you can seek sanctuary in the air conditioned lower level. I wish the audio was a little bit louder on that level due to the sound of the fans and people talking. If you like my reviews, consider "following" my profile for reviews all across the SF Bay Area . Why "follow" someone? It causes the person you follow's reviews to tier to top when you pull up a business. I find this very handy when researching venues. Rod's Review grading scale explained. Essentially I personally base it on the likelihood of a return visit and I try to be stingy with 5 star reviews since they should be "special" in my eyes. Price/Value also play a role obviously but there are $ and $$$$ littered across my grading scale. 5 stars - "I'll go out of my way" (approx 6 % of my reviews) 4 stars- "If I was in the area I'd go here and would recommend", (approx 38% of my reviews) 3 stars "Maybe if was nearby", (approx 37% of my reviews) 2 stars -"Would likely not return, Only if you want to go", (approx 16% of my reviews) 1 star -"No thanks, even if I was hungry", (approx. 3 % of my reviews)

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

    Chicago Detours

    (273 reviews)

    River 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.

    Chicago Private Tours - tours - Updated May 2026

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