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“Lots of great info and stops bring it all to life. Recommend highly. Our guide was full of extra tidbits and interactive.”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“Our guide Matthew was amazing! His storytelling of the Gangsters was great and his knowledge and...again storytelling of yhe historical "ghost"events were tremendous. I am a travel agent and I will definitely be recommending your Gangsters and Ghosts Walking Tour.”
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.
“I was booked in for 10 am I wanted 12 and you couldn't change. cost me a further 40 dollars”
Discover Chicago with an interactive murder mystery tour blending sightseeing, storytelling, and fun detective work. Perfect for history buffs and crime fans alike.
“Cassandra was a great guide! We had lots of fun and learned a lot about Chicago history. 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.
“Great time , guide was amazing . See things that you would never find on your own. The pizza at the end was a nice touch”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“Great tour. Bryson was an amazing guide and storyteller. Despite the cold, it was a fun way to see the city.”
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.
“Joseph is obviously super passionate about this tour. Loved his extra timid bits in between the spiels. Will definitely be recommending this tour to people in the future.”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“Talia was a mega tour guide, so much knowledge and funny. There was just the right amount of food stops/talking - loved it!”
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.
“Tour was amazing. Very informative with a witty blend. Definitely recommend!”
Explore Chicago’s gangster past on a lively minibus tour featuring authentic stories, historic sites, and a humorous guide—perfect for history lovers.
“Marie was super fun and creative! She totally made the tour with her Chicago accent and fun attitude!”
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.
“Wonderful tour. Our guide, Wallach, was very informative and easy to talk with. I’d recommend this experience to anyone interested in Chicago’s history & architecture.”
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.
“Excellent tour. Leah had lots of energy and gave a great tour. Bus was very comfy.”
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.