Experience a colorful side of Chicago history with this gangsters and ghosts tour. With a historian as your guide, you’ll step back to the Roaring Twenties, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Experience the Windy City’s dark past, right in the Loop
Historian guide with expert knowledge of city history
Learn the true tales behind Chicago’s gangster past
Listen to ghost stories and visit spooky haunted sites

What To Expect

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.
1 hour • Admission Ticket Free

Millennium Park

Home to Cloud Gate and a famous Chicago landmark.
15 minutes • Admission Ticket Free

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.
20 minutes • Admission Ticket Free

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.
15 minutes • Admission Ticket Free

Cloud Gate

Will be seen on the tour – also known as “the bean!”
• Admission Ticket Free

The Chicago Theatre

Stop for photos at this famous Chicago landmark!
15 minutes • Admission Ticket Free

The Congress Plaza Hotel & Convention Center

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.
15 minutes • Admission Ticket Free

Highlight

Confirmation will be received at time of booking
Not wheelchair accessible
Near public transportation
Travelers should have a moderate physical fitness level
This tour/activity will have a maximum of 20 travelers

Include

Walking tour of Chicago’s gangsters and ghost stories
Expert Guide

Exclude

Gratuities