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Chicago Mahogany

4.4 (19 reviews)
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Rick P.

Yesterday I had an incredibly educational and fun tour of Pilsen and Little Village hosted by Dilla and Chicago Mahogany. Dilla really knows his stuff and adds such an amazing perspective to Chicago history. I cannot recommend them enough.

Note the small arrow to the right--this denotes that Roseland is the west.
Aesha E.

I've been looking forward to taking one of these tours and I'm pleased I finally have been able to get on the bus! The tour guide, Sherman "Dilla" Thomas, has gained a huge following in Chicago and online in the last couple years. He's an amateur historian who focuses on the south side of Chicago, which is much maligned but has so many hidden jewels and stories that few people want to tell. Dilla is working to fill that gap. The tour I went on was in Pullman, which is a neighborhood that I find pretty fascinating. As a result, I'm fairly familiar with Pullman and even I learned a few things I didn't know. I've been down in Pullman several times but for some reason never noticed that along Champlain (I think it was) the houses change from some of the more typical housing in Pullman to more "typical" Chicago architecture. They aren't new--built in the late 1800's or so--but they are a distinctly different style. What's interesting about them is that they were destroyed at some point in the 19th century and rebuilt, and they are wood frame structures. Chicago has had ordinances against building wood frame homes/buildings since the aftermath of the Great Fire, and these were built 20 years or so later--but they were not in the town of Chicago, since this was still at the time Pullman and yet to be annexed by the city. That was pretty cool to learn! I would have liked to hear more about some of the newlywed housing and housing for single men that was built in Pullman, which wasn't mentioned, but there was a lot of other good content on the tour and some good humor and personality to boot. There are several other tours that CMT does, including one of Bronzeville that I'd be interested in taking sometime. I worked in Bronzeville for 11 years and learned some trivia and tidbits about the neighborhood simply because I went looking for it, but there's certainly a lot more I could learn. There's also a Pilsen one they do, and probably a few more neighborhoods that are far too often neglected by Chicago and the wider world. The tour lasted about 90 minutes or so. It was a bus tour, which was great for the winter months, but I think they're usually by bus. The aisle is super tiny but otherwise it's great that it's something accessible. It's also pretty comfortable.

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8 months ago

This tour was amazing. I could listen to Dilla talk history all day. didnt want it to end.

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4 years ago

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1 year ago

Tour was a great time! Entertaining and incredibly informative. I highly recommend for anyone trying to learn more about Chicago history!

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Review Highlights - Chicago Mahogany

“Dilla is entertaining as hell, blending history with personal stories and experiences into a really fun package.”

Mentioned in 13 reviews

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Family Secrets Tour - Frank Jr

Family Secrets Tour

5.0(67 reviews)
0.8 mi•Near 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!!

Bobby's Bike Hike - Chicago - The best logo in all the land.

Bobby's Bike Hike - Chicago

4.8(1.1k reviews)
0.9 mi•River East, Near North Side

I had a blast at Bobby's Bike Hike!! It was really fun to explore Chicago on our bikes. I really…read moreenjoyed going to the farm in Lincoln park petting zoo, and we got to feed the chickens and pet the goats! You can tell they put a lot of work to make this camp really fun for us! We went to the Chicago Field Museum and spent hours on end splashing in the waves at Ohio Street Beach each day. Our counselors took us on a fun side quest to observe Chicago's sky line from the south side of Chicago's perspective. Our counselors, Matt and Eden were exceptional!! Matt knew a ton about Chicago's history and architecture. He was really engaging and would play football with us. Eden is a natural leader and ensured that kids were safe while having a good time. Overall I had an excellent time at Bobby's Bike Hike.

Chicago Favorites Food & Walking Tour…read more Bottom Line Up Front: Tour: 5 Stars Food: 3.5 Stars Value: 3.5 Stars First of all, the tour was amazing thanks to our tour guide, Braeden. He was super passionate about the city and the food and was a wealth of knowledge on both topics. He also was very charismatic and when he shared stories of Chicago and the food, time flew by. Reflecting on the tour afterwards, my girlfriend and I remembered so many different things we learned because he was so good at keeping things interesting. In terms of the food, we hit the core Chicago staples of deep-dish pizza, roast beef sandwiches, and Chicago-style hotdogs. This was supplemented by a very small bag of popcorn and a small fudge bar. Now I've been on 20+ food tours and for a 3.5 hour tour costing $85, I'm used to 5-6 full food stops with 1-2 small bites compared to the 3 full food stops and 2 small bites, so that fell short. The tour also had an excessively large group with 14 people while many food tours are capped at 10 guests. This led to a few stops selected solely to accomodate a large group that had no significance to being authentically Chicago or foodie-driven like eating the Chicago-style hotdog at the touristy Millenium Hall (3.5 stars on Yelp). If you want to balance both the food and the tour of the city, then I'd recommend this tour for you. However, if you're only in it for the food, there might be better options out there.

Photos
Bobby's Bike Hike - Chicago - Returning from Obama Stimulus tour

Returning from Obama Stimulus tour

Bobby's Bike Hike - Chicago - Biking to the Gold Coast

Biking to the Gold Coast

Bobby's Bike Hike - Chicago - Quality Information

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Quality Information

Charnley-Persky House

Charnley-Persky House

3.3(6 reviews)
1.8 mi•Gold 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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Chicago Mahogany - bustours - Updated October 2026

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