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“Dane was great. He was animated and funny. He made it a great experience. Tips can only be made by cash or venmo”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“I think a tour like this is made by the tour guide and Chris our tour guide was excellent. He was a great storyteller and as a actor who is on a break, he really shows his skills in public speaking and storytelling. He was…”
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.
“Guide-Dane-was great, really enthusiastic. Loved seeing Nittis secret room.”
Discover Chicago with an interactive murder mystery tour blending sightseeing, storytelling, and fun detective work. Perfect for history buffs and crime fans alike.
“If you have a family member who is younger and not much interested in history and architecture, then a little mystery to solve involving actual historical figures will suit the whole family. Plus healthy walking.”
Discover Chicago's dark past on a 2.5-hour night bus tour exploring mobsters, crime scenes, and iconic landmarks with knowledgeable guides.
“John was great and very knowledgeable! Bus was comfortable. And enjoyed all the stops especially the last one!”
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 was a very informative tour led by Alyssa, who is very knowledgeable about all things Chicago!!”
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.
“Knowledgeable and friendly tour guide. Learned a lot about the city and despite being cold we thoroughly enjoyed it. Would highly 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.
“This was a really fun tour that provided a blend of Prohibition era history with tastings of delicious food. Baylor was a great guide and we had a lot of fun learning about the North Side Gang and trying the food. Especially loved the Chicago…”
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.
“Excellent!!! Tour guide was fabulous. She kept you interested and she had a great sense of humor! They really did thier homework. Highly recommended.”
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 guide, Wallach, was excellent. We learned so much about Chicago. Highly recommended.”
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.
“John was our guide and he was so much fun to have leading us through the whole thing! He’s very knowledgeable and made the whole experience fun & interesting! Highly recommend trying this out!”
Discover Chicago's architecture and Prohibition history on this engaging 2.5-hour walking tour featuring insider stories, iconic sights, and local treats.
“Really interesting tour all of it was fascinating. Our tour guide was very knowledgeable and his enthusiasm Chicago and the tour was brilliant”
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.