Chicago Gangsters and Ghosts Walking Tour

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

1. 1

   Chicago Riverwalk

   20 min

   As we cruise along the historic Chicago Riverwalk, look down at the dark waters that hold some of the city's deepest secrets. During the roaring 1920s, this waterfront was the lifeblood of Al Capone’s bootlegging empire

2. 2

   The Chicago Theatre

   20 min

   Snap a photo under one of the most iconic landmarks in the United States—the glowing, six-story-high "CHICAGO" marquee

3. 3

   Palmer House Hilton Historic Lobby

   20 min

   step inside the breathtaking, gold-leafed lobby of the Palmer House, a masterpiece of Gilded Age opulence. While it looks like a royal palace today, this historic hotel holds a dark and legendary past

4. 4

   Cloud Gate

   20 min

   Stand beneath the gleaming, liquid-mercury surface of Cloud Gate—Chicago’s iconic center piecing sculpture

5. 5

   The Art Institute of Chicago

   20 min

   Guarded by its two famous bronze lions, The Art Institute of Chicago is world-renowned for its masterpieces—but it also holds a few spectral secrets.

6. 6

   Stop 6

   20 min

   Prepare yourself as we approach the imposing facade of the Congress Plaza Hotel, widely known as one of the most haunted buildings in Illinois. During the height of Prohibition, notorious mob boss Al Capone practically made this hotel his headquarters

• Wheelchair accessible
• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Transportation options are wheelchair accessible
• All areas and surfaces are wheelchair accessible

For a full refund, cancel at least 24 hours before the scheduled departure time.