Chicago Ghosts and Gangsters Walking Tour

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! Upgrade to the bus tour option to experience the same spine-chilling stories by minibus. Includes one stop for an immersive experience.

Meeting Point

71 E Wacker Dr

71 E Wacker Dr, Chicago, IL 60601, USA

Walking tour meeting location: The tour meets outside of "Hoyt's Tavern", your guide will be waiting for you here!

What's included:

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

What to expect:

Duration: 2 hours

The Loop

Chicago, 60605-2108, Illinois

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.

35 minutes

Millennium Park

Chicago, 60602, Illinois

Home to Cloud Gate and a famous Chicago landmark.

15 minutes

Palmer House Hilton Historic Lobby

17 E Monroe St, Chicago, 60603-5608, Illinois

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

Chicago Riverwalk

22 E Wacker Dr, Chicago, 60601, Illinois

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

Cloud Gate

201 E. Randolph St., Millenium Park, Chicago, 60602, Illinois

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

Pass by without stopping

The Chicago Theatre

175 N State St, , Chicago, 60601-3623, Illinois

Stop for photos at this famous Chicago landmark!

15 minutes

The Congress Plaza Hotel & Convention Center

520 S Michigan Ave, Chicago, IL 60605, USA

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.

5 minutes

Harry Caray's Italian Steakhouse

33 W Kinzie St, Chicago, IL 60654, USA

This is the stop for the bus tour option.

15 minutes