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

Fri 01 Nov

Other dates

You can choose the date already on the booking website

Starting at $35.00

Make a reservation

Fri 01 Nov

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)

REvacationer

Sep 2022

Bailor was our tour guide and she is an excellent speaker, is captivating, fun to listen to and knows a lot! We started a little late waiting for people and Bailor that was running from another tour. Which, unknown to the tour attendees, meant the tour was cut short and we did not make it to the Congress Hotel (bummer). I ended up getting that part of the tour from the Segway tour and it made me go to several sites to get the story. Overall, the tour was excellent and Bailor did a great job. We stopped for 15 minutes at the Palm Hotel and it gave us a chance for a restroom break and to get a brownie (who knew a Brownie was developed in Chicago). I gave it four stars for starting late and missing one of the most haunted places in Chicago. Had those things been corrected, they would have gotten 10 stars!

brittanylQ6053BX

Sep 2022

We had a great tour guide. It was funny, fascinating, and he was great. I really enjoyed this part of my trip. Chicago is beautiful and this was a unique way to explore it.

Rosemary_O

Sep 2022

The guide’s depth of knowledge about the sites gave us fun and interesting insights. I really was amazed that I didn't know about some of the cities greatest tragedies like fires and river accidents.