Gangsters and Ghosts Tour in Chicago

Overview

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.

City: Chicago

Sun 27 Oct

Other dates

You can choose the date already on the booking website

Starting at $35.00

Make a reservation

Sun 27 Oct

Starting at $35.00

Make a reservation

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What's Included

Walking tour of Chicago’s gangsters and ghost stories

Additional Info

Public transportation options are available nearby
Travelers should have at least a moderate level of physical fitness
Face masks required for guides in public areas
Social distancing enforced throughout experience
Regular temperature checks for staff
Contactless payments for gratuities and add-ons
This is a walking tour with limited group size to maintain social distancing.

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.

Millennium Park

Home to Cloud Gate and a famous Chicago landmark.

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.

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.

Cloud Gate

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

The Chicago Theatre

Stop for photos at this famous Chicago landmark!

Show 3 more stops

Cancellation Policy

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

Traveler Photos

Reviews (1000)

geoffp806

Jul 2022

Had a great time on the tour of Chicago's crime history. Would liked to have visited an actual Speakeasy on the tour. The tour guide Kai was very knowledgeable and made the tour fun.

Ronna_W

Jul 2022

Kai was an excellent and informative guide! I learned so much about how prohibition shaped the Chicago crime world.

kimwV7714KS

Jul 2022

Our tour guide, Kai, was great - funny, informative, kept to the schedule, and has a masters degree in history! We were more interested in the ghosts vs gangsters, but I learned quite a few historical things about prohibition and the gang wars and the focus is more on gangsters and a couple of major disasters in Chicago vs more ghosts on other city tours. Had a few sour pus folks on the tour, but it was a good overview of an interesting side of Chicago. And the tour ends in a different spot which is clearly stated in the description, though that is different than some other tours that I have taken. It was an easy walk though down a safe area of Michigan Ave to get back to the Gold Coast (or could have taken a short taxi ride). Thanks!