1. Chicago Gangsters and Ghosts Tours

    1. Chicago Gangsters and Ghosts Tours

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    Chicago Gangsters and Ghosts Tours

    4.7 (463 reviews)
    Open 9:00 am - 10:00 pm

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    Your ends at Congress Hotel
    Josie W.

    Did this tour this past Halloween weekend. Ty was our tour guide and he was great! Very knowledgeable and also cracking jokes along the way. This tour is mainly heavily focused on gangsters, especially Al Capone. They do mention some ghost stories but not as much as I would hope. Maybe Chicago isn't as haunted as I thought it was! They did mention The Devil in the White City which was great (as it is one of my favorite books!) It is a walking tour and it is a very doable walk for everyone. They can modify the tour is exclude stairs in someone in the group cannot walk up stairs, which is very accommodating. Overall, I would recommend this tour to anyone visiting Chicago and wanting to learn for about our gangster history!

    Kelly M.

    We had a nice time with Taka our tour guide on this tour. We saw a lot of really neat things by foot (I don't want to ruin the tour for the person reading this). She had an in depth knowledge and really added a great flair to each story. I would definitely recommend her and this tour for anyone looking to know more of Chicago.

    Sherly H.

    I really enjoyed our night tour with Grant. We walked around Chicago and heard some really neat stories about ghosts and gangsters. We stopped at the Palmer Hotel for a bit and it was really nice. I would recommend this tour to anyone visiting the city!

    Another Street view
    Jennifer C.

    We had a great time this morning on the walking tour. George was our guide. He was fun, friendly, easy to understand, and could raise his voice above the street noise. Totally recommend this. It's about an hour and a half about 2 mi so not super strenuous. Beautiful weather this week too.

    The haunted Congress hotel. Now I want to go there and stay in room for 441!
    Jenna S.

    We took this tour last weekend. Sophie from Louisiana was our tour guide and she was darling.! She was very knowledgeable of the city, and very personable and easy to talk to.! I highly recommend this tour for anybody who has never been to Chicago as well of those who have made multiple trips. Just make sure you wear your walking shoes.

    Gangster activity at the Chicago Theater

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    1 year ago

    Great minibus tour with Avery. Very informative and entertaining tour with a lot of Chicago history.

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    2 years ago

    A really fun guide yay Sarah! We learned a lot about Chicago and gangster history on a beautiful day in our fair city

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    2 years ago

    Great tour! Max was phenomenal. It was cold but he did such a good job I forgot about the Cold!

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    2 years ago

    Taka, our guide was awesome!!! Lucked out on great weather! We both loved every minute!

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    Chicago Gangsters and Ghosts Tours Reviews in Other Languages

    Ask the Community - Chicago Gangsters and Ghosts Tours

    Is this tour wheelchair accessible?

    We crossed a few streets and briefly went inside a hotel (which was more of an intermission). I would say the whole tour could be accessed with a wheelchair. Just to prepare, arrive a bit early and talk to the guides. They were very helpful, and if… 

    Where does this tour end? Wondering where to park.

    Ours ended across the street from the Congress Hotel. Note: That’s not where it started.

    How long is the tour?

    The tour was 1.5-2 hours wirh 15 min break. The tour is walking threw Dt chicago

    Don’t See Your Question? Ask Away!

    Review Highlights - Chicago Gangsters and Ghosts Tours

    It was interesting hearing about some of Chicago's darker history and the life of Al Capone and his crew.

    Mentioned in 30 reviews

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    Family Secrets Tour - Frank Jr

    Family Secrets Tour

    5.0(66 reviews)
    0.5 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!!

    Shoreline Sightseeing - Chicago Fire Department near Navy Pier

    Shoreline Sightseeing

    4.7(1.9k reviews)
    0.8 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!

    Photos
    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

    Charnley-Persky House

    Charnley-Persky House

    3.3(6 reviews)
    1.4 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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    Wendella Tours & Cruises - Chicago River Architecture Tour

    Wendella Tours & Cruises

    4.4(1.6k reviews)
    0.1 miNear North Side

    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!

    90 minute Architecture tour…read more It was a cloudy, windy, and cold day in June. Even with the clouds rolling in & out and blocking a lot of the views it was still interesting and our awesome guide, Bobby, was knowledgeable, funny, and kept it interesting and flowing for adults and kids. The tour starts on the river heading towards Lake Michigan. The ride into the lock was a little lengthy as we had to wait for them to fill it with boats first. Once we made it onto Lake Michigan it was very chilly, but I'd rather be freezing than sweating like crazy on a hot humid day. We were on a smaller boat which was nice. - upper deck: Seats long the outside and chairs in the middle. Only wish they had cushions. - lower deck: had some small seating outside and standing bar tables - lower deck: indoor restrooms and bar area - snacks, drinks available for purchase If rain is in the forecast bring paper towels to clean off your seats. I also saw some people with Wendella rain ponchos, but not sure where to get them? Really fun and beautiful way to see the city! Highly recommend!

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

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    Chicago Gangsters and Ghosts Tours - historicaltours - Updated July 2026

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