No city in America owns its criminal history quite like Chicago does. The Prohibition era here wasn’t just bootleggers and tommy guns — it was a full-blown shadow economy that touched politicians, judges, priests, and your neighbor’s grandmother. Chicago became the testing ground for organized crime in America, and the stories that came out of it are so specific, so strange, and so deeply local that most people leave this tour genuinely rethinking everything they thought they knew about the 1920s and beyond.

This one is a little different from a typical walking tour, and that’s exactly the point. You’ll settle in and let our resident crime and gangster expert take you deep into the world of Al Capone, Dean O’Banion, Bugs Moran, Machine Gun Jack McGurn, and Sam Giancana — not as caricatures, but as real people operating inside a real and ruthless system. You’ll learn what the Beer Wars actually were, who was outsmarting whom, which murders were personal and which were just business, and why a flower shop and a tailor became some of the most notorious addresses in Chicago history. It’s part history lecture, part storytelling, and completely gripping from start to finish.

This tour is free to join — our guides work for tips, and we suggest $15 to $25 per person if you feel the tour delivered. The lecture format means you’re comfortable and out of the elements no matter what Chicago’s weather decides to do that day. Wear whatever you like, show up curious, and get ready to hear Chicago tell on itself.