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

Mon 28 Oct

Other dates

You can choose the date already on the booking website

Starting at $35.00

Make a reservation

Mon 28 Oct

Starting at $35.00

Make a reservation

New York City Tours

Unique Activities (21) Transfers & Transportation (103) Tours, Sightseeing & Cruises (113) Entry Tickets (47) Sporting Events (1) Good for Small Groups (6) Seasonal & Holiday Tours (41) Walking Tours (697) Outdoor Activities (20) Limitied Availability Tours (6) LGBT Friendly Tours (4) Family-friendly Activities (7) Solo Travelers' Tours (147) Food & Drinks (27) Travelers recommend (73) Good for Groups (8) Top Activities (18) Guided Audio Tours (3) Art, Culture & History (135) Attractions to explore (38)

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)

Jennifer J

Jul 2022

Rosa was a great tour guide! Fun way to explore the loop area. My only complaint is that the tour ends in a different location then it begins.

AliCas1980

Jul 2022

A friend and I were visiting Chicago and decided to take this tour for the interesting history we may learn (plus alleged ghost stories, which are fun, but less important). Our guide was a kind man who clearly loves this job. With that being said, it was obvious he was reciting a script as opposed to telling us a real story. His delivery was patronizing in that it felt as if he was talking to middle schoolers on a field trip as opposed to adults. There were no children in our group, so this delivery was puzzling at best, cringey and disingenuous at worst. The history given wasn't anything one couldn't find with a cursory Google search. My friend and I left the tour during the break at the one-hour mark. We would have left sooner, however, we wanted to be respectful to the guide and not walk away while he was talking. Overall, this tour ended up being a waste of time and money that I can never get back. Skip it and take the architecture boat tour or other history tours of the city.

vincentdG7041XJ

Jul 2022

We really enjoyed this tour while on a recent vacation to Chicago. Great history of the city with a lot of fun and interesting facts about the Prohibition era of Chicago. Our guide, Lizzie was the best - she was very knowledgeable and interactive with the group. I highly recommend to anyone visiting the city. Great exercise too - it's a nice walk around town.