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“Tour guide was great. Locations were less than exciting. Interesting little mob museum, and we even went back to our discount at the restaurant later that day. Tour guide was the hit of the experience. Great personality, and fun, upbeat attitude.”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“Alan was great, enthusiastic and informative guide. Was well worth the money, great way to explore Chicago and would highly recommend”
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.
“Leah Nicole was amazing , warm, friendly , funny, extremely informative. Was in town for a conference and was looking for a fun activity with a colleague. We were NOT disappointed AT ALL. Learned a mix of crime history, architecture, and Chicago trivia in a…”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“Guide tried hard but he can only play with the cards he is dealt. There would appear to be little left of 20s Chicago so the gangster part was pretty brief compared to what I hoped for. No mention of Dion O’Bannion or John Dillinger…”
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.
“My husband and I had a great time on this tour. Our guide David was very knowledgeable and passionate. The buildings were spectacular and the true crime stories were wild.”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“Alan was great! He spoke clearly and made the experience great!”
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.
“John was great! Tour was packed with knowledge but presented in a casual fun way that kept everyone engaged!”
Explore Chicago’s gangster past on a lively minibus tour featuring authentic stories, historic sites, and a humorous guide—perfect for history lovers.
“The host was very knowledgeable and entertaining. The tour was comfortable and enabled us to learn about that era.”
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.
“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.”
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.
“The tour guide was knowledgeable, patient and informative”
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.
“According to my two teenage boys, this was the best part of their first visit to Chicago.”
Discover Chicago's architecture and Prohibition history on this engaging 2.5-hour walking tour featuring insider stories, iconic sights, and local treats.
“We had a great time learning about the architectural history and sights of Chicago with Rich! He was very knowledgeable and had lots of interesting details about each of the places we visited.”
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.
“I think maybe more mob based”
The river runs through an architecture lesson, and the lake applauds.