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    Weird Chicago Tours

    3.9 (194 reviews)
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    death alley
    Jess P.

    Not something I would normally do, but I'm visiting, and it was offered as an option at the conference I was attending. That said, it's a fun, tourist entertainment experience. Our guide, Eric, brought us to sites of disaster, burial grounds, gang violence, serial killers, and mass death. He had impeccable timing with his delivery and gallows humor, and was a repository of weird historical information. I might have made different choices as far as where the bus stopped (the mausoleum or John Hancock building would have been spookier than the empty parking lot), but Eric made all of the sites interesting and engaging for the group. They allowed beer on the tour, which was great, and they offer other tours, like a focus on mob violence or serial killers.

    Museum of Science & Industry
    Rachel W.

    We had a great time with our guide, Eric, on "The Devil & The White City" tour. He enthusiastically and passionately gave a lot of great Chicago history. The tour could have easily lasted another hour and I don't think anyone would have minded. A few sites on the tour included The Rookery, Congress Hotel, Chicago Fire Academy, Chicago Stockyards (which I found to be the most eery), 63rd & Wallace (Murder Castle site) & Jackson Park. I highly recommend Weird Chicago Tours (particularly this one) to anyone visiting the area or even Chicago natives. These definitely aren't your typical tours of Chicago. Would love to return for the Serial Killer tour. Well worth the $.

    George J.

    Did the Devil in the White City tour with my girlfriend.We recently did the tour; it was 8 degrees out. Brrr. We found the tour to be well-paced. Our tour guide, Eric, was very knowledgeable, and enthusiastic about the material. Fortunately, Eric didn't keep us outside too long. Interesting fact. Each tour guide writes their own tour. So no two tours are ever the same. In the future, I would suggest incorporating a bathroom stop.

    Our first stop...Pretty for it being the site where over 800 pple died, right? *cue dramatic music*
    Connie L.

    I thoroughly enjoyed this tour. My mom and I picked the haunted history tour and we were not disappointed. We learned about and were brought to the locations of the Eastland disaster that killed over 800 pple, an upscale theater that was locked from within and killed a couple hundred, a peaceful looking park which actually sits on an UNEMPTIED cemetery, a hotel that gangsters used as a gathering location AND happened to be the site where infamous serial killer H.H. Holmes used to abduct victims...those are some teasers. We visited mainly downtown and north Chicago areas. How cheesy or corny does the haunted theme get? Yea, I know what you mean. Some pple really enjoy ghost histories or sightings/stories, even if some of it seems dramatized. Personally, I do believe in spirits/ghosts, but I'm not that eager to actually find them and I'm not that into taking pics to see if I get some floating head in the pic. I would say this tour was a good balance to the spectrum of ghost believers. Even if you don't believe in ghosts/hauntings, it's a pretty decent history tour if you like learning about the darker side of Chicago history. And for those who are ghost hunters, our guide was excellent and actually was a ghost hunter for 12 years prior. She encouraged photos and questions. Most of the tours are at night; the upsides are that the city isn't as crowded, the atmosphere is better for our theme, and it's a cool way to end the day. The downsides are that it can be pretty tiring after a long day to have the energy to pay attention, going into the winter months it can get pretty windy/cold, and you're gonna feel like some kid again sitting on a yellow school bus roaming around the city They've got different tours themes you can choose from - from focusing on haunted areas in Chicago, to mob/crime locations, to prohibition/red light district. Would definitely recommend!

    Tara H.

    Wonderfully weird tour of Chicago based on Devil in the White City! The tour guide was knowledgeable & entertaining! He made it easy to imagine what it was like to have attended The World's Fair! Although the chartered school bus used for the tour was a bit cramped, it did provide a nostalgic field trip vibe, LoL. You'll see parts of Chicago you may not see otherwise like the site of the former H.H. Holmes "Castle", The Stockyards, Midway Plaisance, Garden of the Phoenix & so much more! Hear stories of the demented life & mind of H.H. Holmes - America's 1st serial killer, intertwined with awe inspiring tales of the events, exhibitions and complicated creation of The World's Fair! I highly recommend this tour if you are looking to learn about a different side of the White City & the devil that terrorized it during The World's Fair.

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    Page 1 of 5

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    Review Highlights - Weird Chicago Tours

    The tour guide we had, Ken, took us to the site of the Eastland disaster, the old Chicago gallows, and a few other places.

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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.

    Weird Chicago Tours - tours - Updated May 2026

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