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“Very informative. Harry Caray’s place was awesome. The different stops were really cool as well. I would recommend to anyone interested in Chicago crime history.”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“Oh my gosh, we absolutely loved our tour! Max was beyond amazing! As native Chicagoans looking for a Valentine’s Day to remember, this experience totally blew us away! It’s wild—we realized we knew so little about our own city that we actually felt like tourists…”
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.
“Jay was a great tour guide! Really informative! Really enjoyed the tour!! The bus was quite loud and squeaky and it was hard to hear even with her speaker on full volume!”
Discover Chicago with an interactive murder mystery tour blending sightseeing, storytelling, and fun detective work. Perfect for history buffs and crime fans alike.
“Great way to learn about Chicago in an interactive way. The walking tour allowed a view of multiple neighborhoods, the beach, and ended right by the Drake hotel.”
Discover Chicago's dark past on a 2.5-hour night bus tour exploring mobsters, crime scenes, and iconic landmarks with knowledgeable guides.
“I grew up watching all the mob, gangster movies. This tour did not disappoint. John had a wealth of information. It was fun to start the tour learning that Streeter was from Flint, as I grew up right outside of Flint. I highly recommend.”
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.
“Great tour guide was really knowledgeable! Had a lot of fun and learned a lot of cool things! 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.
“We absolutely loved our tour with Alan! The experience was amazing from start to finish, completely exceeding our expectations. Alan was friendly, fun, and you can really tell he loves what he does. He showed us incredible spots around the city, always patient and attentive…”
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.
“Jonathan was excellent as our guide. Super knowledgeable and enthusiastic about the subject matter. Highly recommend this tour.”
Explore Chicago’s gangster past on a lively minibus tour featuring authentic stories, historic sites, and a humorous guide—perfect for history lovers.
“Bus tour with gangster history delivered with fact and humor. Most of the sites are no longer present. Tour of many city neighborhoods to cover the North, South, West gangs.”
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 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 Prohibition history and stunning architecture on a small-group walking tour, exploring landmarks, cultural spots, and local treats for an authentic experience.
“Rich was a great tour guide, he was very knowledgeable and it a great tour of Chicago highlights”
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.
“Javier was an amazing guide. The experience was informative, fun and a unique perspective on the City.”
Discover Chicago's architecture and Prohibition history on this engaging 2.5-hour walking tour featuring insider stories, iconic sights, and local treats.
“The tour guide was on time, patient and understanding. He was kind and accommodating. The tour was done in a bit of a rush and we didn’t enjoy the tour as much as we could have. It was a small group of two couples- it…”
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.