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.
“This tour was good cool information about the city's history, our tour guide Adam was very funny and attentive throughout would definitely 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.
“The Chicago Crime and Mob Tour was such a fun and fascinating experience! It was full of stories I’d never heard before — ones that really brought the city’s history to life and added a whole new level to my short stay in Chicago. The…”
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.
“This tour was very informative, professional and humorous. Began on time and ended with a nice surprise. Highly recommend to anyone wanting some back stories about the Chicago mob history.”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“Tyson was a fantastic guide! Very knowledgeable with a side of humor! The tour was well worth it! Our family continues to talk about what we learned!”
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.
“This tour was fascinating and Joseph was such an engaging tour guide! A majority of the tour was spent inside looking at interior architecture, with brief walks outside to get to the next destination (much appreciated on this 10 degree winter day!) Would definitely book…”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“The guide Payton was really nice and we had a lovely tour with her. For food there was some steak, a slice of Deep dish pizza and then also chicago hotdog. We were really full afterwards. So there was also enough to eat. And we…”
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 a great tor guide. Had a lot of fun. And very informative. Would recommend to everyone! 10/10”
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.
“ASK FOR LARA! Such a great tour! Our tour guide Lara was the best! She was funny, witty, spunky & her background as a teacher was the cherry on top! FOOD was delicious and FILLING! If for whatever supernatural reason you’re not full by the…”
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 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 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.
“My gf and I had the best tour with Dave. He knew so many hidden spots and all the history we were interested in. Highly highly recommend”
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.