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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. Guests of the  tour will have the rare opportunity to visit some of these famous haunted locations and old crime scenes throughout Chicago’s downtown. Places like the haunted Congress Hotel, Death Alley and the Palmer House will all be visited along this tour. Bring your camera because you never know when you might see a ghost!

This tour 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.

Tour Length and Distance

This is a 2 – 2.5 hour walking tour through the loop area of the city’s downtown district. The tour is about 1.5 miles long with frequents stops and a refreshment/restroom break.

Tour Time and Meeting Location

The tour meets at 8 p.m. nightly next to the Wyndham Grand Riverfront Hotel at 73 E. Upper Wacker Drive on the corner of Wacker Drive and N. Wabash.

Locations visited
Chicago Private Tours and Productions
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
  • Experience the dark past of one of Chicago’s most frequented areas, the Loop
  • Historian guide with expert knowledge of city history
  • Learn the true tales behind Chicago’s gangster past
  • Listen to ghost stories and visit spooky haunted sites
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1 - 5 of 20 reviews
Reviewed yesterday via mobile
Great way to spend an evening

We really enjoyed the tour. Our guide was Lauren and she was very informative and entertaining to listen to. This is a great tour for anyone interested in history and would like to know more about Chicago. We would recommend this tour.

Thank Slinkcat
Reviewed yesterday
Very fun and informative

Our guide Dylan was funny and very knowledgeable! Highly recommend! We walked quite a bit, wear comfortable shoes

Thank Susan N
Reviewed 1 week ago
History, Tragedy, Ghosts and Gangsters

This is about a 2 hour 1.5 mile walking tour through the Loop area that takes you to some of the locations of Chicago's worst tragedies and gangster murder locations that occured from the late 1800's until the prohibition era and a few beyond that....More

Thank Bill K
Reviewed 2 weeks ago via mobile
Nice stroll

My wife and I booked the 8pm tour with Stephan as our guide. I like smaller group tours and this was just that. A group of 10 walked to different notable sites of crime and unfortunate history for residents of Chicago. Stephan was personable and...More

Thank Tim O
Reviewed 3 weeks ago via mobile
Gangsters and Ghosts Tour

The Gangsters and Ghosts Tour was one of the things I was most looking forward to on my recent trip to Chicago and it definitely didn’t disappoint! Our tour guide Stefan was fantastic, very engaging and clearly very knowledgeable. We visited some really interesting sites...More

Thank Jemma L
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Questions & Answers
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Lark R
28 June 2018|
Response from Mal B | Reviewed this property |
Get a cab, we were staying at the Publishing House B&B on Washington St out in the West Link cab fair was $6 plus tip and there were plenty of cabs available
Andree J
18 June 2018|
AnswerShow all 2 answers
Response from Kristine P | Reviewed this property |
I don't think so, it was all on the sidewalks. There was one place down by the river but I've got to think they have ramps...
2 June 2018|
Response from Kristine P | Reviewed this property |
I'm not aware of any age restrictions.
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