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    Route 66 Chicago

    4.5 (4 reviews)
    Open 9:00 am - 7:00 pm

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    Chicago Architecture Center

    Chicago Architecture Center

    4.8(814 reviews)
    2.7 kmThe Loop

    chicago architecture center boat tour on the "the first lady" was well done. very rainy day but a…read morechoice of remaining upstairs out in the open, where we were given a big umbrella which was nice, or some of our group went downstairs out of the rain. liz our docent was so knowledgable and informing, 11 out of 10 for her.

    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)

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    Chicago Architecture Center
    Chicago Architecture Center
    Chicago Architecture Center - Amazing right?

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    Amazing right?

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

    Chicago Detours

    4.9(273 reviews)
    2.6 kmRiver 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.

    Family Secrets Tour - Frank Jr

    Family Secrets Tour

    5.0(66 reviews)
    2.7 kmNear North Side

    Just went on the tour today. Frank is a really nice man and the tour is Great fun. Entertaining and…read moreI was totally captivated by the stories. There's other "Mob" tours but this is one where the guy giving the tour was actually there. He grew up with all these people around him and his family. Along with his book which I also highly recommend, I would say the entire tale is fascinating and I cannot wait for it to be a movie. After the tour you really feel empathy for what this guy and his family was put through as a result of the mafia street life. If you're visiting the city, or if you are a local, take this tour, you'll love it!

    This was probably one of the best tours I've been on, and my fiancé (who has very high standards…read moreabout these things) agrees. We booked a tour for Saturday at 2 pm. There were some technical difficulties and the TV system on the bus ended up not working. Mr. Frank Calabrese Jr was very professional and good-humored about the situation. He offered everyone on the bus the opportunity to come back free of charge so that we may have the full experience with the photos he had been intending to show us. He proceeded to do the tour without the presentation, which honestly was great in itself. He is a very good story-teller, and had a great narrative. He had notes with him but only referenced them a few times to make sure he wasn't forgetting anything. Everything was super authentic and off the cuff. I loved that we went around Chicago and we were able to get glimpses of how the city was like in the 60s-90s. What made this tour so great was that these stories were first-hand. It didn't come from someone who spent hours studying the history; this was his real life. He was very genuine about his experiences, and his anecdote about his kids at the very end of the tour made me tear up a bit. He even invited us to stay for happy hour at the Chop House to have a drink with him to talk. I would highly recommend this tour to anyone, regardless of whether you know the mob history or not. I personally didn't know too much, and still was captivated by his stories. He does have a book (which I definitely intend to read) and a movie in the works!

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    Family Secrets Tour - Aftermath of the car bomb attached to the underside of Michael Cagnoni's silver 1979 Mercedes-Benz.

    Aftermath of the car bomb attached to the underside of Michael Cagnoni's silver 1979 Mercedes-Benz.

    Family Secrets Tour - Assistant State's Attorney William H. McSwiggin a.k.a. "Hangman Prosecuter"

    Assistant State's Attorney William H. McSwiggin a.k.a. "Hangman Prosecuter"

    Family Secrets Tour - Tina Cruz and Liz Cote with Frank!!

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    Tina Cruz and Liz Cote with Frank!!

    Gray Line Sightseeing Tours - View from our Lincoln Park stop over looking the beautiful Chicago skyline (Scenic North Side Tour)

    Gray Line Sightseeing Tours

    2.3(68 reviews)
    2.3 kmThe Loop

    This company did not provide the services I paid for due to employees who have no idea what they…read moreare doing. if I could give zero I would. Specifically, I ONLY went back to Dubai to go to the Louvre in Abu Dhabi because it was not open on my first trip. I selected the tour that provided this and it was all set up for Sunday. Without asking me someone changed my tour ( I did not consent to this change) to Monday'; the museum is not open on Mondays. i was told this was a mistake but since I only went to see this museum this was a MONUMENTAL MISTAKE. I took off work, paid for their services and flew to Dubai for a specific reason. I did not get to see the museum, not because it was a holiday or it was under maintence but because some employee had no idea what they were doing. When I complained and asked for a partial refund since I did not get what I paid for, I was offered a free trip to Abu Dhabi when I come back to Dubai. This is unacceptable since i have no intention of returning to Dubai any time soon or know if I ever will. This is a very large company and while mistakes happen, the cost for me should not be so high. They screwed up a trip I carefully set up for my purpose due to incompetence and then refuse to accept responsibility. Be very careful in choosing this company for dream vacations because they could get messed up and then they will do nothing about it

    Candace is the best driver and tour guide. She made our ride entertaining and fun. She puts her…read morewhole heart in her job. She new passenger by name. We had trivia questions and prizes.

    Photos
    Gray Line Sightseeing Tours - Abraham Lincoln Statue

    Abraham Lincoln Statue

    Gray Line Sightseeing Tours - Buckingham Fountain

    Buckingham Fountain

    Gray Line Sightseeing Tours - Chinatown

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    Chinatown

    Chicago River Boat Architecture Tours - Our boat

    Chicago River Boat Architecture Tours

    4.7(285 reviews)
    3.4 kmNear North Side

    Highly recommend!…read more Easy to book online. Came in early June, 12:00pm reservation. I had booked a tour a year before but had to cancel last minute due to illness and they refunded me 100% the day before. Line started 30 minutes before the departure time so get there early if you want a specific spot. Chairs on top as well as some benches on the side. Seating area downstairs, bar, and complimentary water, lemonade, coffee/ tea. Nice bathrooms on board. Ed was an amazing tour guide, very knowledgeable and Chicago local who knows his history of the city!! Informative and funny! *Note: This is the only tour I've been on so I have nothing to compare it too. Some of the other tours looked bigger, I would probably try another one next time just to compare.

    Chicago riverboat architectural historical tour on main branch of river. Time to cruise…read more Nonstop 90 minutes. Talk about the architectural sky scraper wonders. foremost. Mind blowing enormously tall. Alot of humor and details on rental price @$400,000 a year. Famous people like Barack Obama and Oprah Winfrey lived here. Willis seats tower 100 stories tall 1,052 in the Windy City Sky! It's the tallest! there are 37 drawbridges on the main branch river. That's all the facts in my head could remember. The river is alive! The buildings taller than Sequoia redwood trees or Oregon Douglas Fir. Glass, concrete and steel in assorted shapes - seemingly alive like a living tree. I feel the energy of the river and the buildings standing tall. Worth the moolah.

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    Chicago River Boat Architecture Tours - Boat top floor

    Boat top floor

    Chicago River Boat Architecture Tours
    Chicago River Boat Architecture Tours

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    Medieval Torture Museum  - Flagel Pillory

    Medieval Torture Museum

    4.4(207 reviews)
    2.3 kmThe Loop

    Very amazing tour! Shows the punishments of the medieval times and the pain and suffering inflictedread more

    Who knew there were so many ways to be tortured throughout history? That was my takeaway from…read morevisiting the Medieval Torture Museum in the heart of the Loop. Looking on their website, there are other torture museum outposts in Florida, California, Branson (MO), and Berlin, Germany in addition to Chicago. The Chicago location is on the compact side, but packs over 100 medieval artifacts into dimly-lighted, macabre space occupying two levels. My timing for visiting was right around Halloween. I purchased tickets online (can get a very slight discount buying online) for a friend's belated birthday. He had always wanted to see this space, and we had scheduled an outing here, followed by happy hour libations. My interactions with the front-desk/check-in personnel (a younger gentleman and a woman getting off of her shift) were pleasant and professional. The young man mentioned that he was studying art. I'm sure this museum gave him plenty of inspiration. To the side of the check-in/welcome area there is a souvenir shop. I didn't really see anything that grabbed me, but there were a couple of promotions taking place and the displays/signage were memorable and lighthearted, considering the grim subject matter. Before making our way to the exhibit, we cued up the audio guide on our phones. The guide is easily accessible through Apple and Android, although I wish I had brought headphones, as I quailed at blasting the sound through speakers with other patrons around. Fortunately, this is more of a selfie and photography-geared space, so there were no dirty looks as I would have expected in a traditional museum or gallery. This museum has something for everyone, whether one is an avid reader of all of the informational material around the exhibits (raises hand) or prefers a more interactive, hands-on experience and photo-ops to capture the thrills and chills. Among the most arresting items are a torture rack from 15th-century Spain and a life-size replica of Joan of Arc being burned at the stake. Over the sound system, occasionally dramatized screams and creaking chains play to heighten the creepy ambiance. All told, it took around an hour to peruse the space, sharing impressions and taking photos.

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    Medieval Torture Museum  - Medieval Torture Museum

    Medieval Torture Museum

    Medieval Torture Museum  - Torture

    Torture

    Medieval Torture Museum  - We all have that 1 coworker

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    We all have that 1 coworker

    Chicago Fireboat Tours - View of city

    Chicago Fireboat Tours

    4.9(65 reviews)
    3.5 kmThe Loop

    A beautiful day on the Lake Michigan. Had a blast on Veteran-owned FIREBOAT-TOURS today! Such a fun…read moreafternoon soaking up Chicago's history and architecture from the water. The itself was comfy and solid, and it's pretty cool to think this fireboat served the city's fire department from 1937 to 1981. Lucky us, we caught a perfect day light winds and clear blue skies. Thank you to Cliff, our tour guide, who had serious knowledge of Chicago history and a fun vibe was fabulous. The bartender, magic manning, was a total character, bringing good energy and making sure everyone had a good time. In fact, the whole crew was super welcoming and made the experience even better. Next time we are going to try the sunset cruise and do this all over again.

    Think Jeopardy-Chicago edition. Cliff is an excellent narrator and will give you information you…read morenever realized you wanted ...or needed. We learned about the architectural features of the beautiful buildings. The historical Chicago fires. Movie trivia. Why Chicago is really called " The Windy City" and why Manhattan got its name for good measure. Guess which building sits on a landfill. Why the lake is cleaner than its ever been. Experience a boat lock. The history the fire boat played in Chicago's history. Our party of 5 took the 3 pm trip on Memorial Weekend. It was a beautiful, beautiful day. Our boat was comfortable and not as crowded as all of the other tours we passed. It is a veteran owned business. Tours begin Patrick's Day through October! "May you have fair winds and fortunate seas!"

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    Chicago Fireboat Tours
    Chicago Fireboat Tours
    Chicago Fireboat Tours - Skyline views

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    Skyline views

    Route 66 Chicago - historicaltours - Updated June 2026

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