Gangsters and Ghosts Tour in Chicago

Combine a history lesson with supernatural tales for an ideal Chicago activity! Hear about Chicago in the roaring 1920’s when speakeasies in The Loop attracted notorious gangsters including Al Capone, with lively commentary from your historian guide!

Go back in time on the Gangsters and Ghosts tour to hear about Chicago in the roaring 1920’s! See former gangster hangouts and haunted places like Congress Hotel, Palmer House, and Death Alley.

We proudly host a 2-hour, 1.5-mile walking guided tour that explores the gangsters and ghosts of Chicago’s past in the area of “The Loop.” Known as the vice district during the 1920s and 30s shady partying, deal-making, and threats, riddled with speakeasy saloons, secret underground tunnels used by bootleggers, and the famous Al Capone, The Loop is where the understanding and depiction of the 20th century gangster began.

Hosted by historians, it is not a theatrical guided tour; rather, the stories are told in a more intimate setting that really paints a picture for guests of Chicago’s past. Spooky, real tales of the ghosts of Chicago’s streets will be shared along the route. Family friendly and accommodating in nature, the tour makes frequent stops with a refreshment and restroom break.