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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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    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

    My family and I had such a wonderful time with Wendella Tours and Cruises! Even though the weather…read morewasn't perfect, it actually made our adventure even more special. The friendly and knowledgeable staff went above and beyond to make us feel comfortable, including cleaning the seats for us. Our tour guide was so well-informed and kept us dry, which was really impressive. They even had $5 rain ponchos for sale. The boat had two floors, and those who preferred a more private space could also buy drinks like free spirits and alcoholic beverages. Since this was my very first trip to Chicago, I definitely want to join the tour again. The price was fair, the staff was warm and welcoming, and the relaxed atmosphere made the whole experience even more enjoyable. Plus, I learned so much! Overall, my family had a fantastic time, and we wholeheartedly recommend it!

    First time on the architecture boat tour on the recommendation of a bunch of friends who had…read morealready taken the tour in the past. Personally, I was pleasantly surprised. The words "architecture" and "boat tour" don't immediately spell a fun time in my mind. But this tour is 1) a pleasant way to see the center of Chicago from the water, 2) actually interestingly informational, as the tour guides are extremely on top of their game, 3) much more dense that you expect (these guys are talking non-stop), and 4) surprisingly good views, especially when you get all the way out into the edge of the harbor! Finding the place was a bit roundabout, but once we got there, staff were super friendly, and it was easy to get on the boat and off to our next stop afterwards. Parking suggestions on the site are solid too. I'm not sure whether I'd do it again, but I'd definitely recommend it as a must-do stop on any visit!

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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(688 reviews)
    0.8 miRiver East, Near North Side

    Yes,Chef Chicago Food Tour. Our tour guide Casey was great! He was friendly, knowledgeable and make…read morethe tour fun. We had 29 people on our tour. Had a hard time getting a seat to eat at Mr Beef. Very hot and crowded. PizzaLobo portions very small and hardly any cheese on the pizza. Publican Meats. They put out a charcuterie board that was very skimpy. Cheese and Pate. Did not even have enough pate for everyone. Several people did not even get one. This was due to others taking several. They were very small. No room and very cramped quarters too. We felt we filled up on the strawberry donut on the next stop. For the price we paid, it would have been nice to have bigger portions on the main food and not the sweets.

    My wife and I had an amazing time on the Yes, Chef! Chicago: A Bear-Inspired Food Tour. Our guide,…read morePhilip Winston, truly made the experience memorable. Dressed in a white T-shirt and blue apron--just like the chefs from The Bear--he immediately set the tone for the tour. His enthusiasm was contagious, and throughout the experience he shared fascinating facts, behind-the-scenes stories, and local anecdotes that kept everyone engaged from start to finish. At each stop, the food was ready and quickly distributed, so we spent more time enjoying the experience and less time waiting. Every sample was delicious and showcased why Chicago has such an incredible food scene. Whether you're a fan of The Bear, a foodie, or simply looking for a fun way to explore Chicago's culinary culture, I highly recommend this tour. And if you're lucky enough to have Philip Winston as your guide, you're in for an outstanding experience!

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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.

    Shoreline Sightseeing - Chicago Fire Department near Navy Pier

    Shoreline Sightseeing

    4.7(1.9k reviews)
    1.1 miNear North Side

    Eric was a very good speaker and staff war very nice, the entire thing was very informative thank…read moreyou guys so much!

    This tour was on the top 10 list of our things to do in Chicago. I researched all the boat…read morecompanies that offered the Chicago architecture boat cruises and Shoreline Sightseeing came out hands down #1 for us in tour length, type of cruises, accessibility and in price for what you got. Best deal. Our tour guide was happy, energetic, and very knowledgeable about Chicago because he was born and raised there. We chose the 75 minute, 4pm Chicago River tour and it covered a lot! We never lost interest and learned about Chicago's history. It is well worth it! Our Architecture River Tour boat departed from the dock at Navy Pier. We learned that their boats are the most accessible at this location. Their boats can accommodate wheelchairs up to 30-inches wide. Your wheelchair must be able to navigate a ramp with a 2-inch step at one end. I needed one that was kind to my knees. Best to call them for more details. They were very helpful whenever we called them. Their boats are both double-decker and single-level boats, and there is generally no protection from the sun, rain, or wind. There is a small bar on the main level. Restrooms are located on the lower deck, which is accessible only via stairs from the upper deck. Enjoy! It's amazing!

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    Shoreline Sightseeing - The Chicago Architecture Tour boat cruise was amazing!

    The Chicago Architecture Tour boat cruise was amazing!

    Shoreline Sightseeing - Top deck - guide Joe

    Top deck - guide Joe

    Shoreline Sightseeing - Merchandise mart

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    Merchandise mart

    Weird Chicago Tours - tours - Updated August 2026

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