Gangsters and Ghosts Tour in Chicago

2025 Ratings
  • Live Guide
  • Instant Confirmation
  • Group Tour
  • E-Ticket
  • 2 hr

Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago! You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive.

Itinerary Details

This is a typical itinerary for this product

Stop At: The Loop

The area most associated with gangster era crime and haunting is know as “The Loop”. This was the cities vice district during the roaring 20’s and 1930’s riddled with speakeasy saloons, secret underground tunnels used by bootleggers and the headquarters of famous gangsters such as Al Capone. The tour is about 1.5 miles long with frequents stops and a refreshment/restroom break.

Duration: 1 hour

Stop At: Millennium Park

Home to Cloud Gate and a famous Chicago landmark.

Duration: 15 minutes

Stop At: Palmer House Hilton Historic Lobby

Stop for a break at the Palmer House Hotel, rumored to be haunted. The Palmer House Hotel is the oldest hotel in Chicago and considered the oldest continuously operating hotel in the USA.

Duration: 20 minutes

Stop At: Chicago Riverwalk

You'll walk along the Riverwalk during the tour, which is guided by a Historian. It is not theatrical, but rather the tales are told in a more “around the campfire” fashion. Spooky and verified ghost stories will be shared throughout the tour along with visiting the famous gangster hang outs.

Duration: 15 minutes

Pass By: Cloud Gate

Will be seen on the tour - also known as "the bean!"

Stop At: The Chicago Theatre

Stop for photos at this famous Chicago landmark!

Duration: 15 minutes

Stop At:

Tour ends at the Congress hotel, named one of the most haunted places in the State of Illinois. Al Capone set up his headquarters here, and his ghost is most frequently seen near his old suite on the 8th floor.

Duration: 15 minutes
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