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    Gray Line Sightseeing Tours

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

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    8 years ago

    Great tour of the north side. Mitch was great and super funny! Unbelievable how he drives that bus on those city streets.

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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.

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    Family Secrets Tour - Frank Jr

    Family Secrets Tour

    5.0(66 reviews)
    0.9 miNear North Side

    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!

    I'm a huge fan of true crime and Chicago history, so I'm surprised to say that this was my first…read morecrime tour ever. But everything happens for a reason, and it seems that reason was that I was meant to wait until the perfect one came along -- that, my friends, happened to be the Family Secrets Tour. I met Mr. Calabrese Jr. weeks ago when he presented some of his intriguing life stories at an event at Chicago Chop House, and I knew that evening that I had to book and experience the real deal, aka his bus tours. My friend and I booked a tour for a Friday afternoon recently that started at 2pm, and though there was a bit of a delay because our bus's TV monitors weren't working, Mr. Calabrese Jr. smoothly filled the time with some behind-the-scenes stories he said he usually doesn't share on the tour. I was hooked immediately. To be honest, before this tour, I had no idea the stories his family was involved in were so high-profile (I even talked to my family afterward, and they ALL knew every detail and were mad I didn't invite them! Sorry family!). But even while he showed us news clips, a lot of photos, and told all of his stories, he remained modest, which made the entire experience endearing. Mr. Calabrese Jr. is super charismatic and a great storyteller, and you can tell he genuinely loves telling his story and showing everyone around the neighborhoods where he grew up, and where big moments happened in history to people who were in "the life." I truly enjoyed this tour and I recommend it for anyone who wants an real, honest, non-theatrical recap of Chicago's mob history. The Family Secrets Tour is engaging and delightful. Thank you so much for captivating us, Frank! Can't wait to bring my family along some time!

    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(813 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?

    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 May 2026

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