Chicago · GANGSTER & MOB TOURS
Capone, Dillinger, the Biograph and a garage on North Clark Street. These 15 tours differ on whether you walk or ride, how much is standing at plaques and how much is real research — priced, timed and honest about which are family-safe.
Chicago Loop bootleggers, ghosts, and Al Capone lore, guided by a historian. Walk key landmarks, plus optional minibus upgrade.
“Taka was our guide and she was fantastic. We had such a good time, she was a very good story teller, loud and clear. Lots of interesting information. We learned alot and had a lot of fun.”
Ride Chicago by coach to the St. Valentine’s Day Massacre, Dillinger sites, and mob haunts. Live guide, photo stops, mini museum included.
“Incredibly interesting and such a cool tour!! Our tour director Maddie is a fantastic story teller and it was so cool to learn who all these people were. 2nd time in Chicago and learned more on this tour than anything else! Highly recommend!”
Chicago South Loop gangsters and ghosts guided walk with a historian, inside hotel stops, Riverwalk and Death Alley stories, 2 hours.
“Bailor was our guide and she’s the best! Super interesting and fun. We were happy to learn new things of Chicago.”
Chicago mob and crime bus tour with Dillinger sites, St. Valentine's Day Massacre, and Frank Nitti museum, 90 minutes.
“Lots of information to digest. Nice being able to get off the bus. Our guide was great.”
Prohibition tales plus Chicago classics on a 2-hour small-group walk featuring steak, Chicago dawg, and deep dish stops.
“Loved learning the history of the Irish North and Italian South gangs and the clever ways they stuck it to each other. Pizza was phenomenal, and Harry Carrys basement was so interesting with the tunnels!”
A mob and haunt walking tour through Chicago’s Loop, with eerie hotel stories, the Alley of Death, and guided history for $34.
“Great experience! Our guide, Justin, was very entertaining and knowledgeable. The walking was not extensive.”
Chicago gangster lore meets food tastings in River North on a 2-hour walk. Three stops include deep dish pizza, steak, and a hot dog.
“our guide Baylor was very knowledgeable about the sites we visited and was an overall great guide. All the food was also really good, the mix of eating and walking around was really comfortable since it was not a very long distance between stops.”
Chicago Prohibition speakeasy bus or walking tour with a guide, 3 to 4 historic stops, and drink recommendations to buy along the way.
“Really authentic tour guide with has a nice storytelling way to tell about the prohibition in general but specifically in Chicago. Especially nice were the fotos and the access to the Harry Carays premises”
A small-group Chicago mob history bus tour with a costumed guide, climate-controlled comfort, and key stops tied to Dillinger and O’Banion.
“Excellent!!! Tour guide was fabulous. She kept you interested and she had a great sense of humor! They really did thier homework. Highly recommended.”
Prohibition-era Chicago in 2.5 hours, walking from Chicago Theatre to Millennium Park with iconic architecture, Riverwalk stops, and popcorn.
“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.”
Chicago Loop walking tour linking Prohibition culture to standout architecture, ending at the Bean with skyline views and popcorn.
“The cultural center tour was fantastic. The explanation was educational. It was billed as a prohibition tour but the information on that topic was limited.”
A 1.5-hour Chicago River night cruise with spooky gangster tales, Eastland and Chicago Fire stories, plus skyline views from Tribune to Willis.
Haunted Ghosts and the Chicago Outfit Segway tour glides through Chicago’s fires, gangster tales, and night landmarks in about 2 hours.
“Great experience! Really great guides - informative and good training for how to use the segways. Really enjoyable, would definitely do it again!”
A 90-minute Chicago Gangsters and Movies Tour linking mob legends to major filming locations from the Riverwalk to the Cultural Center.
“Really interesting and informative, Andre was also very happy to answer questions. Lots of fun, would highly recommend”
2-hour Chicago Loop gangsters and ghosts minibus tour with skyline views, Prohibition-era stops, and ghost stories for $49.
“The tour guide was very informative. Very sweet. It was a fun and amazing experience. Glad we had this opportunity. Everything was timed perfectly.”
Every kind of day out in the city, and the best of each.
