Chicago Gangsters and Ghosts Walking Tour

346 Reviews |

Recommended by 95% of reviewers

|

Badge of Excellence | Chicago, USA

2 hours (approx.)

Mobile ticket

Offered in: English

Instant confirmation

Overview

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn.

Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers.

Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business".

Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

What's Included

Visits inside the Palmer House
Historian guide
Guided walking tour

Gratuities

Meeting Location

Meeting point

71 East Wacker Drive
Chicago, IL 60601, USA

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Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

520 South Michigan Avenue
Chicago, IL 60605, USA

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.

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Chicago Riverwalk

As we cruise along the historic Chicago Riverwalk, look down at the dark waters that hold some of the city's deepest secrets. During the roaring 1920s, this waterfront was the lifeblood of Al Capone’s bootlegging empire

20 minutes Admission Ticket Free

The Chicago Theatre

Snap a photo under one of the most iconic landmarks in the United States—the glowing, six-story-high "CHICAGO" marquee

20 minutes Admission Ticket Free

Palmer House Hilton Historic Lobby

step inside the breathtaking, gold-leafed lobby of the Palmer House, a masterpiece of Gilded Age opulence. While it looks like a royal palace today, this historic hotel holds a dark and legendary past

20 minutes Admission Ticket Free

Cloud Gate

Stand beneath the gleaming, liquid-mercury surface of Cloud Gate—Chicago’s iconic center piecing sculpture

20 minutes Admission Ticket Free

The Art Institute of Chicago

Guarded by its two famous bronze lions, The Art Institute of Chicago is world-renowned for its masterpieces—but it also holds a few spectral secrets.

20 minutes Admission Ticket Free

The Congress Plaza Hotel & Convention Center

Prepare yourself as we approach the imposing facade of the Congress Plaza Hotel, widely known as one of the most haunted buildings in Illinois. During the height of Prohibition, notorious mob boss Al Capone practically made this hotel his headquarters

20 minutes Admission Ticket Free

Show 5 more stops

Additional Info

Confirmation is instant and will be received at time of booking
Wheelchair accessible
Transportation options are wheelchair accessible
All areas and surfaces are wheelchair accessible
Service animals allowed

Public transportation options are available nearby
Suitable for all physical fitness levels
Infants and small children can ride in a pram or stroller
This tour/activity will have a maximum of 25 travelers

Frequently Asked Questions (8)

Q: What is the cancellation policy for the Chicago Gangsters and Ghosts Walking Tour?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CST).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-5669845P1

Traveler Photos

Reviews

4.83

346 reviews

Average 4.83 out of 5 stars based on 346 traveler reviews collected by Key West Private Charters and partner sites such as Cool Destinations and TripAdvisor

5 stars

313

4 stars

17

3 stars

9

2 stars

3

1 star

4

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