Chicago · GANGSTER & MOB TOURS
16 reviewed
Al Capone ran this city, and the sites are still on the map. These mob tours take in the St. Valentine's Day Massacre corner, the old speakeasies, and the hotels the Outfit worked from. Here is which travel by bus and which on foot, how long each runs, and what to book.
A 2-hour Loop walk blending prohibition gangland lore with reported hauntings, led by a historian and ending at Congress Plaza.
“Taka was our guide and she was fantastic! The stories were interesting, her directions were clear, she kept the group on time, and she projected her voice and spoke very clearly in a large group on loud city streets. We would definitely recommend this tour!”
Chicago Crime and Mob Bus Tour whisks you through Capone-era streets with a live guide, photo stops, and a mini mob museum for $49.
“Had a blast with our tour guide Sofia. Thank you for the tour and the laughs. The coach was roomy and comfortable. We had a great time!”
2-hour South Loop walking tour with a historian guide for gangster stories, ghost legends, and haunted hotel stops at Palmer House and Congress Plaza.
“Our guide Chris was very clear & easy to understand. Excellent as my husband has a hearing issue, and had no problem hearing & communicating with him. He was informative & entertaining.”
Chicago mob crime bus tour with St. Valentine’s Day Massacre, Dillinger’s last steps, and a mini museum. 90 minutes, $49.
“Jay was our guide and she was great! My partner and I highly recommend this tour.”
Solve a murder while walking Chicago’s Magnificent Mile, Gold Coast mansions, and the lakefront. Mugshot photos included.
“A great adventure of history and storytelling as you walk through Chicago’s neighborhoods. Fun for all ages to learn about those who previously strolled along these streets.”
Chicago Night Crimes Tour by bus delivers a fast-paced look at mob history, St. Valentine’s Day Massacre, tunnels, and river views.
“Great tour, lots of interesting information! The guide was knowledgeable and entertaining. We loved the stops.”
A 2-hour Chicago River North gangster-and-food walk with steakhouse tunnels, deep-dish pizza, and iconic hot dog stops for $79.
“Taka is a great story teller! We throughly enjoyed our time exploring the city with a fun gangster twist and food. Loved the Chicago Hot Dog the best!”
A small-group mob and ghosts walking tour through Chicago’s Loop, from the haunted Congress Plaza to Capone-linked haunts.
“This tour doesn’t match the description. The content was informative but it seemed fragmented. You had to make your own connections to the theme. Left with unanswered questions.”
A $35 Chicago Loop walking tour that pairs historic architecture with true crime stories, with lots of indoor stops and great photo timing.
“Super fun and interesting tour. We joined at the last minute as something to do while in Chicago for the day. Saw a lot of different buildings and learned about the history and architecture. Plus a perfect blend of creepy murder history as well.”
2-hour River North walk with three tastings, deep dish, steak and a Chicago hot dog, plus Capone hideouts and a Prohibition tunnel.
“Guide was very knowledgeable, answered any questions. Tour was very entertaining and funny at times . Would definitely recommend this tour which included fabulous tasting food, great stories and value for money . Cracking tour Thank you Alan”
A $48, 1h45 Chicago mob tour by climate-controlled minibus with a costumed guide, big city stories, and stops like 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.”
A 2-hour Chicago night crime tour by luxury bus. See the St. Valentine’s Massacre site, Dillinger’s last steps, and Nitti’s safe.
“VERY VERY INTERESTING THE WHOLE TIME!!! AWESOME!!! Def Recommend!!! book early!!”
Chicago River night cruise with gangster and horror stories at twilight, plus landmark skyline views. 1.5 hours, $45, drinks for sale.
Haunted Ghosts & The Chicago Outfit Segway Tour: learn to ride fast, hear chilling Chicago stories, and zip through night-lit landmarks.
“We were stuck in traffic and in danger of being late to the tour but the guides and staff were super nice and promised to make sure we were not disappointed. We did manage to arrive in the nick of time so no accomodation was needed after all. The segway tour was so much fun we are already looking forward to the next one.”
A 90-minute Chicago walking tour linking mob history with major movie scenes, guided by Andre, with souvenir photos included for $35.
“Really interesting and informative, Andre was also very happy to answer questions. Lots of fun, would highly recommend”
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