Gangsters and Ghost Tours

Interested in the secret pursuits of mobsters, hoodlums and even ghosts? Then Chicago is the right place for you! Get a two in one tour that features dark occurrences in the shadows: both the criminal underworld as well as the world of strange happenings related to the paranormal.   

Bootleggers and criminals, such as the disreputable Al Capone, are featured in this exciting and informative tour of one of America’s favorite cities with a seedy past. Offering guided walking tours based on nefarious history and shocking events, Gangsters and Ghosts Tours tells stories and secrets of infamous happenings, underground activities and illegal endeavors throughout the two-hour outing.

Visitors to Chicago won’t want to miss out on the opportunity to immerse themselves in the “City of Bullets”, a nickname referring to the criminal history of Chicago’s past. Even natives of the city can glean interesting information and see old sites from a new perspective by taking a look at the darker side. Guests on this exploration will follow in the footsteps of some scandalous characters, such as Scarface, while hearing hair-raising stories of death by fire, or tales of a “Murder Castle”.

Types of Gangsters and Ghost Tours

Offering a non-theatrical crime tour that encompasses approximately 1 ½ miles, Gangsters and Ghosts Tours are focused on the thing that they know best—Chicago’s dark and ominous history. Tours are hosted by knowledgeable historians who share stories to paint a picture of the sinister world of the windy city’s past. Spooky tales of gangsters and ghosts along the streets and in the buildings of Chicago are told as the tour group stops at famous locations in the Chicago Loop Vice District.

What You’ll See on a Gangsters and Ghost Tour

Exploring the Chicago Loop Vice District, Gangsters and Ghosts tour groups typically meet at the Wyndham Grand Riverfront Hotel and spend time walking throughout the local area. The district got its name during the ‘20s and ‘30s when the area was riddled with speakeasy saloons, secret underground tunnels and shady deal-making.

Guests of the tour will visit various crimes scenes and haunted locations where all kinds of infamous activities happened a century ago, including:

  • The Congress Hotel—constructed in 1893, the visitation site of the ghost of Dr. Henry H. Holmes, Chicago’s first serial murderer
  • Death Alley—also known as Couch Place, this location is where more than 600 people fell or were trampled to death as they tried to escape a fire in the theater next door
  • Palmer House—iconic for its importance during days of big bands and jazz starlets
  • Chicago Athletic Association—just down the street from Al Capone’s former headquarters
  • Gangsters and Ghosts Tours typically end at the Congress Hotel

Gangsters and Ghost Tours Services

Gangsters and Ghosts Tours provides public, live-narrated historic walking tours several times a day throughout the summer months.

Gangsters and Ghost Tours Timing

Gangsters and Ghosts Tours last for approximately 2 hours each and several tours run each day, all year round. Check the company website for a calendar and available dates.  

Gangsters and Ghost Tours Considerations

Answers to questions you might have before taking a Gangsters and Ghosts Tour:

  • Cameras are not only allowed, but are recommended—because you never know when you might see a ghost!
  • Tours are family friendly and make frequent stops for restrooms and refreshment breaks
  • Children of any age are welcome and may receive discounted tickets. Children under the age of 6 years old may be complementary.
  • Meeting location is typically at Wyndham Grand Riverfront Hotel, 71 E Upper Wacker Drive (on the corner of Wacker Drive and N Wabash).
  • This 1 ½ mile tour encompasses a fair amount of walking. Participants should wear comfortable walking shoes.
  • Tours run rain-or-shine which means that guests should dress appropriately for the weather, bringing a sweater or jacket along during cooler months.
  • For an added amount of spooky fun, choose an evening tour when it’s dark outside!
  • Unfortunately, Gangsters and Ghosts tours are not wheelchair accessible due to the nature of the locations visited.
  • This tour typically hosts a group of approximately 15 people, making it small and intimate.
  • Refunds of booked tickets may be possible 24 hours or more prior to the start date of the experience.
  • Tours tend to sell out, especially during summer months, so be sure to book tickets well in advance of your preferred day.
  • These tours typically end in a different place than where they began. Guests should be sure they understand how to return to their car or hotel from the ending location. Guides are happy to help with this information.

Book a Gangsters and Ghost Tour

Tickets for Gangsters and Ghost Tours should be purchased in advance online. Tours often sell out. Booking with is easy online. Online bookings show weekly availability including tour times as well as revealing tours that are already sold out. Pay for your tour in advance with a credit card and receive an email with all of the information you need about where and when tours meet as well as what to expect.

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