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“Great narration about mobsters. Only stop to get out of bus to see where John Dillinger was killed and Frank Nitti’s vault.”
Discover Chicago’s dark past with this 2-hour guided walking tour exploring gangsters, ghosts, and haunted landmarks in the South Loop district.
“It was excellent!! Max was very informative and really made it so much fun!!”
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.
“Great tour with wonderful tour guide. Lots of fun. The tour successfully wove a modern mystery with architecture and history of Streeterville, Gold Coast and Michigan ave,”
Discover Chicago's dark past on a 2.5-hour night bus tour exploring mobsters, crime scenes, and iconic landmarks with knowledgeable guides.
“Great tour, lots of interesting information! The guide was knowledgeable and entertaining. We loved the stops.”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“Ben was exceptional, energetic and full of knowledge. I loved listening to him talk. Had a wonderful time.”
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.
“Get ready to have your mind blown on so many real facts on Chicago architecture! You will get your steps in while listening to some bone chilling events!”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“Our guide Taka was great. She made the tour an interesting and tasty experience”
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.
“Jonathon was SO knowledgeable!! All of the tour narration was so captivating and informative! I will say, though, that he did not need to use such “ foul language “ throughout. He was charming, fun, and a great guide, but that language did not enhance…”
Explore Chicago’s gangster past on a lively minibus tour featuring authentic stories, historic sites, and a humorous guide—perfect for history lovers.
“Maria was our tour guide. We boarded the bus to a flapper, dressed young Chicago woman who had an amazing sense of humor, witty, and was an excellent historian. We absolutely loved our tour and have not stopped talking about it. When other friends of…”
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.
“Kelly, our guide, was phenomenal! We live in the Chicagoland suburbs so thought to take an official tour to learn more details than the obvious ones we already knew. Kelly fulfilled that with much knowledge, grace and charm. Had a wonderful tour and learned a…”
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 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 criminal past on a 2-hour night tour. Explore famous crime scenes, learn about mobsters like Al Capone, and enjoy authentic local insights.
“Great information and knowledge and loved being able to view the sites were amazing.”
Discover Chicago's architecture and Prohibition history on this engaging 2.5-hour walking tour featuring insider stories, iconic sights, and local treats.
“We can see most of the main landmarks of the city, which has an impressive architecture and it is beautiful! Guide Rich is very attentive and helpful, a lovely person!”
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.