Chicago Gangsters and Ghosts Walking Tour 2 hr

Walk through Chicago’s South Loop, where stories of gangsters and ghosts linger among grand hotels, theaters, and historic streets. On this 120-minute Chicago Gangsters and Ghosts Walking Tour, a historian guide brings the city’s past to life with true accounts of its notorious characters and haunted corners.

Explore a neighborhood once known as a vice district during the 1920s and 1930s, when underground speakeasies, secret tunnels, and bootleggers shaped its reputation. Hear about Al Capone and the places where gangsters gathered, made deals, and conducted business. Along the way, discover ghost stories associated with the Chicago Riverwalk and Death Alley, and visit inside the Palmer House. The route also takes you past the Chicago Theatre before ending outside the Congress Hotel, described as one of Illinois’ most haunted places.

Meet your guide outside Hoyt’s Tavern 15 minutes before departure. With accessible areas and a historian’s perspective, this Chicago Gangsters and Ghosts Walking Tour offers a vivid look at the city’s darker history. Join the walk and see what stories emerge around the next corner.