Chicago
The Capone-era circuits: mob-and-crime bus tours past the massacre sites, prohibition speakeasy crawls and murder-mystery nights that lean into the archive. Chicago’s underworld history is its best-documented export; the tours cite their sources.
Discover Chicago’s notorious crime past on this engaging 1.5-2 hour coach tour, exploring famous mob sites, crime scenes, and historic landmarks.
Most Popular“The tour is well organized and the guide was extremely knowledgeable and funny! I would highly recommend this!”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“Baylor was an excellent guide all around, knowledgeable and funny. This is a nice walking tour around the Loop downtown, takes about 1.5 hours. It was great to see the architecture and an added bonus that we were able to take inspiration of places to…”
Discover Chicago’s criminal past on a 1.5-hour Mob and Crime Bus Tour. See infamous crime scenes, learn about legendary mobsters, and enjoy authentic stories.
“Excellent tour . Ethan presents it really well and brings the gangster era back to life”
Discover Chicago with an interactive murder mystery tour blending sightseeing, storytelling, and fun detective work. Perfect for history buffs and crime fans alike.
“The door was a lot of fun and very informative. The Tour Guide is a great storyteller and entertainer. Would definitely recommend!”
Discover Chicago's dark past on a 2.5-hour night bus tour exploring mobsters, crime scenes, and iconic landmarks with knowledgeable guides.
“I loved it.The story teller was knowledgeable and entertaining. We really needed more time at Harry Carey's. There wasn't enough time to see the tunnels and use the restrooms.”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“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.”
Discover Chicago's stunning architecture and dark crime stories on this engaging 1.5-hour walking tour led by passionate guides exploring iconic buildings and hidden pasts.
“Great tour! Joseph was very informative and gave a great tour hitting all the highlights. Also stops inside a lot which is nice for the cold days. Would definitely recommend!”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“Peyton was a great host. Really interesting and knowledgable. The tour was fantastic with lots of lovely food.”
Discover Chicago's Prohibition era on a guided speakeasy tour—choose walking or bus options, visit historic bars, and learn about gangsters, politicans, and more.
“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”
Explore Chicago’s gangster past on a lively minibus tour featuring authentic stories, historic sites, and a humorous guide—perfect for history lovers.
“Tour guide was great. Very interesting tour. Good review of the city mob areas. A stop midway through the tour would be nice.”
Discover Chicago’s history, architecture, and hidden gems on a 2.5-hour walking tour exploring Prohibition, Millennium Park, and iconic buildings with expert guides.
“Tour was great. I highly recomend it for a first experience in Chicago. Richard was an excellent guide and gave lots of great advice and tips.”
Discover Chicago’s Prohibition history and stunning architecture on a small-group walking tour, exploring landmarks, cultural spots, and local treats for an authentic experience.
“Our guide Kevin was full of very interesting facts and stores, really felt like we got to know the city. Might have been just 30 minutes too long as we were tired at the end”
Discover Chicago’s criminal past on a 2-hour night tour. Explore famous crime scenes, learn about mobsters like Al Capone, and enjoy authentic local insights.
“John was our guide. He clearly loved his history and was funny with it. The bus was very nice. Our tour was interesting and fun. We enjoyed the whole thing.”
Discover Chicago's architecture and Prohibition history on this engaging 2.5-hour walking tour featuring insider stories, iconic sights, and local treats.
“The former library is beautiful. The stops were informative. Overall it was the right amount of time for a walking tour.”
Discover Chicago's dark past and stunning skyline on a 1.5-hour twilight river cruise filled with stories of mobsters, fires, and mysterious sightings.
“Beautiful skyline. The volume was perfect.”
The river runs through an architecture lesson, and the lake applauds.