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    Weird Chicago Tours

    3.9 (193 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!

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    Ken B.

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    Ask the Community - Weird Chicago Tours

    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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    Wendella Tours & Cruises - Chicago River Architecture Tour

    Wendella Tours & Cruises

    4.4(1.6k reviews)
    0.4 miNear North Side

    The Lake Fireworks tour was excellent. Gabby was our guide and she was excellent and very…read moreknowledgeable. The tour combined fireworks, history, and architectur. The whole family loved it.

    I've been to Chicago many times, but never did the architectural boat tour thinking 'oh it's too…read moretouristy.' This time I gave in thinking the weather is nice and I want to do something relaxing. Wendella was highly ranked and a friend recommended them. I was bummed when I saw the 90 minute sunset tour was sold out. I saved $50. lol I was happy to find that they had a 45 minute tour at 8pm. This was actually perfect and for $28! I got to see a little bit of light when we boarded and the actual sun setting and views of the city in the dark. Very beautiful. The host tries to tell us history and be funny, but I think most were busy taking photos or just relaxing as a breeze hit. The ride is smooth so not to worry if you typically get motion sick. I felt fine. You may book tickets online and I'd show up by 7-7:15pm to get on the 8pm boat. The line gets long and if you want premium seating in the back or along the sides, then you want to be early. This 45 minute tour takes off a little bit further in than the 90 min one that has entry just off the bridge by Michigan Ave. Not sure if the boat had a restroom. Overall I'd budget about 2ish hours for this activity from the time waiting in line, cruise, and getting off the boat. Highly recommend!

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    Wendella Tours & Cruises
    Wendella Tours & Cruises
    Wendella Tours & Cruises

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    Chicago Food & City Tours - Urban Belly caramelized chicken dumplings

    Chicago Food & City Tours

    4.8(691 reviews)
    0.8 miRiver East, Near North Side

    My 13 year old daughter and I enjoyed the Iconic Foods of Chicago tour yesterday. Our guide Lillian…read morewas fantastic! the food was all amazing and I especially enjoyed all of the history she shared about the foods and neighborhoods of Chicago. Highly recommend!

    Amazing amazing amazing! My best friend and I absolutely loved the "Yes Chef! Chicago: A Bear…read moreInspired Food Tour". Casey, our guide, was phenomenal. So fun and witty, and he really went above and beyond to make sure we had a great experience. All the places we visited were very special and iconic, including a bakery that's 115 years old and an ice cream shop that's 105 years old. It was really fun remembering where these places appeared in the show. Another perk of the tour was skipping lines and having special areas and service just for us. And not having to drive and look for parking. The air conditioned bus was lovely and comfortable, and it was fabulous to be driven around different neighborhoods. We went to so many great places and it's a fun way to get to know the city better. We ate so much good food!!! Italian beef sandwich, charcuterie, pepperoni pizza, hot fudge sundae, strawberry donut and more. Great drinks too! Beer and cocktails, or soda. I didn't need to eat for the rest of the day! Everything was delicious! I highly recommend this tour! It was exceptional and worth every penny.

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    Chicago Food & City Tours - Mr. Beef beef sandwich with hot peppers

    Mr. Beef beef sandwich with hot peppers

    Chicago Food & City Tours - Pizza Lobo pepperoni pizza

    Pizza Lobo pepperoni pizza

    Chicago Food & City Tours - Our tour guide in a local temple.

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    Our tour guide in a local temple.

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

    Chicago Detours

    4.9(272 reviews)
    1.1 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.

    Weird Chicago Tours - tours - Updated August 2026

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