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.
“Great! Even in cold winter the walk was very enjoyable. Our guide Max was also very attentive and cheerful; We will ask for her again in our next visit soon. Hopefully not so cold!”
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.
“Really great tour guide who told us so much history and entertaining stories about Chicago crime history. We had a few stops for photos but otherwise, this was mostly on the bus which was fine considering the amount of ground we covered! Definitely recommend for…”
Discover Chicago with an interactive murder mystery tour blending sightseeing, storytelling, and fun detective work. Perfect for history buffs and crime fans alike.
“This was so much fun for everyone! We learned more history than I expected to in a fun way and saw new spots even though we have all been to Chicago several times.”
Discover Chicago's dark past on a 2.5-hour night bus tour exploring mobsters, crime scenes, and iconic landmarks with knowledgeable guides.
“Had an amazing time on this tour!!!! Hearing the stories and stoping at some of the same locations these gangsters and outlaws actually visited , stood, worked and even lost their lives at was quite the experience! The bus driver and tour guide were very…”
Explore Chicago's dark side with this mob and haunt walking tour. Discover haunted hotels, mob hangouts, and supernatural stories for an authentic experience.
“Knowledgeable guide, relevant topics covered made an enjoyable night out for locals and tourists alike”
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.
“Good walking tour. Owner is building his business and shows enthusiasm for that! He is knowledgeable about the history and a Chicago native. Thank you!”
Discover Chicago’s gangster past and iconic foods on this 2-hour walking tour with tastings, historic hideouts, and stories of Capone’s era.
“It was fun, entertaining, and informative. Talia was so knowledgeable and passionate. I would recommend this tour to everyone. And I had my first hotdog with a sport pepper. So good!”
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.
“We had so much fun and learned so much about Chicago’s speakeasy and mob scene! Our tour guide was laid back and great, very knowledgeable. We had great drinks along the way from 3 very different places. We enjoyed the whole 3 hours very much…”
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.
“I had the absolute pleasure of touring Chicago with Dash, and it was nothing short of phenomenal. Dash didn’t just recite facts—he brought the city’s architectural heritage and hidden treasures to life with a depth of knowledge and a genuine passion that made every moment…”
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.
“Excellent tour. Dash is very knowledgeable and taught us a lot. He’s very cognizant of the groups needs for breaks, restroom and snacks. He shows and educates us on local treats.”
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.
“It was a great and informative tour. Really learned a lot about the culture and architecture history of the city. The chocolate and popcorn tasting was an additional plus.”
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.