Chicago · CHICAGO GANGSTER & PROHIBITION TOURS
25 tours
Capone’s Chicago is mostly parking lots and rebuilt frontages now, which is exactly why you want someone pointing at them. These tours run the Prohibition addresses, the speakeasies that survived and the corners where the famous shootings happened, on foot and by bus, with prices and run times.
Chicago Loop gangster tales and ghost stories on a 2-hour historian walk. Millennium Park, Palmer House, Riverwalk, and Capone legends.
“Very exotic experience, another good way to know about Chicago history beside just regular tourist spots”
Ride Chicago by coach on a crime-and-mob tour with comedy-bent storytelling, photo stops, and a mini mob museum for $49.
“Our host Dane was energetic and entertaining! We learned a lot on the tour and enjoyed the stops. Would recommend to those wanting to know more about Chicago history!”
A 2-hour Chicago South Loop walk mixing Al Capone era stories and ghost legends, with stops at iconic landmarks and hotel interiors.
“Sophia was a delight! This was my favorite tour of this trip. So much knowledge and lore crammed into 2 hours. A must for true crime, history, and ghost story fans.”
90 minutes on a comfy Chicago mob bus. See the St. Valentine’s Massacre site, Dillinger steps, Frank Nitti artifacts, tunnels, and a quiz.
“Great tour with lots if interesting fact. If you like the mob you’ll enjoy the tour”
Solve a Chicago murder mystery on a guided walking game through Water Tower, the Magnificent Mile, Gold Coast, and Oak Street Beach.
“Super fun small-group way to learn about the city’s history and see some of the Mag Mile and Gold Coast. We took our 9 year old and he had an easy time keeping up with the walking and the history / mystery.”
Prohibition-era gangster stories plus Chicago classics in a small-group 2-hour food walk for $79, from River North to the Gold Coast.
“We booked this tour for a client and they absolutely loved it! They could not say enough good things about their tour guide, Avery. He was so knowledgeable about the city's history, the architecture, and they said that he was the reason they had such a great tiRead more”
Chicago Loop architecture and true crime walking tour. Palmer House lobby to Chase Tower, ending near Christkindlmarket.
“The guide was great and very knowledgeable. The tour was informative and we saw some cool buildings.!”
Chicago gangs and iconic bites on a 2-hour River North walk with three tastings, Capone hideouts, and deep dish pizza.
“The guide Payton was really nice and we had a lovely tour with her. For food there was some steak, a slice of Deep dish pizza and then also chicago hotdog. We were really full afterwards. So there was also enough to eat. And we enjoyed the stories about the gangsters.”
Chicago Prohibition speakeasy tour with 3-4 guided stops, downtown walking or neighborhood bus. Drink tips, mob-era stories.
“This was without doubt the very BEST experience we had in Chicago - and we did every single tourist trip available. Job was hilarious - dry, so knowledgeable and so passionate about the city and its history. A MUST for any visitor to Chicago.”
Chicago mob tour by minibus with costumed, funny storytelling, climate control, and a close look at key sites like Holy Name Cathedral.
“The tour guide was knowledgeable and funny. I thought we would get out of the vehicle to explore some sites but as it turns out through no fault of the company, many of the sites are not there anymore or they are privately owned businesses that you couldn't go into anyway. Still the tour was very interesting, and again the tour guide was fun”
Prohibition-era Chicago walking tour with Riverwalk architecture, Chicago Cultural Center, popcorn tasting, and Millennium Park and the Bean in 2.5 hours.
“Our tour guide Bash was outstanding. He enthusiastically shared his love for Chicago and its history. This is a must tour for first timers to Chicago. We learned so much about the history, architecture and people who made Chicago.”
A 2.5-hour Chicago Loop walk linking Prohibition-era clues to world-class architecture, ending at Millennium Park’s Bean and Cloud Gate.
“Very informative and interesting. Dave was easy to be with and was a wealth of information. We would never have known about these things or seen as many interesting points if we hadn’t taken this tour”
A 1.5-hour Chicago River night cruise with darker stories, mob-era tales, and skyline views around famous downtown landmarks for $45.
A 90-minute walking tour linking Chicago gangsters to famous movie scenes, with Andre’s stories and souvenir photos at seven landmarks.
“Had a really enjoyable tour with a small group which was great, Andre was very knowledgable & filled us in with loads of interesting facts & info. We struggled to find the meeting point, it was outside The Chase building, just up from the Chicago Cinema if you need a landmark.”
See Chicago Loop gangster and ghost legends by minibus in about 2 hours, with a skyline view, haunted stops, and Harry Caray entry included.
“Overall interesting commentary from a knowledgeable tour guide. Excellent value for the money and also got to see a great skyline photo opp view of Chicago.”
