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    Gray Line Sightseeing Tours

    2.3 (68 reviews)
    Closed 9:00 am - 5:00 pm

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    Review Highlights - Gray Line Sightseeing Tours

    The Gray Line Trolley worked out pretty well for us as a mode of transportation around the city of Chicago on a Sunday.

    Mentioned in 2 reviews

    Read more highlights

    Family Secrets Tour - Frank Jr

    Family Secrets Tour

    5.0(66 reviews)
    0.9 miNear 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!

    Photos
    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!!

    Chicago Architecture Center

    Chicago Architecture Center

    4.8(812 reviews)
    0.5 miThe 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 River Boat Architecture Tours - Our boat

    Chicago River Boat Architecture Tours

    4.7(285 reviews)
    0.8 miNear 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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    Charnley-Persky House

    Charnley-Persky House

    3.3(6 reviews)
    1.8 miGold Coast, Near North Side

    One of the many Frank Lloyd Wright houses on our list, we bought tickets while in town…read more I will say apart from the house being somewhat contradictory to many attributes that make up a Wright design, the house was very nice. The tour however was probably one of the weakest I have been to. Our guide was forgetful and really didn't go over the basics with the house as we are accustomed to with Wright tours: commission of the home, Wright himself, change of hands with home, and while walking thru it- design aspects chosen inside the home. There's three levels - you only get to see two, and the second floor is currently an office so it is hard to get a real feel for the place. Easily the weakest tour we have been on

    I love the work of Louis Sullivan and Frank Lloyd Wright, so touring this house made perfect since…read moreas both were involved in its design. The mansion is located in a gorgeous corner of the Gold Coast and represents an important part of the city's architectural story. That being said, it's not the most impressive historic house I've ever been in. In fact, it wasn't the most impressive one I went in on that day. For me, the things that made this tour worth doing were the small details like the windows, doors, wood screen in the hallway, and the fireplace surround. There aren't many rooms and the furnishings are not original. The textured walls seem odd and the lighting has been altered in several places (like he sconces). The tour guide was very knowledgeable, but they don't know much about the original owners due to their private nature. The building is now used as offices, so the upstairs bedrooms contain desks and bookshelves rather than being set as they were intended. It takes some imagination when you walk though them. The house is only open two days a week - Wed and Sat. I bought tickets I advance, but you can probably get them in person most times. I'm glad I went, it the friend who accompanied me thought it wasn't as impressive as the other houses we toured that afternoon.

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    Charnley-Persky House
    Charnley-Persky House
    Charnley-Persky House

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    Gray Line Sightseeing Tours - historicaltours - Updated June 2026

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