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Gangsters and Ghosts Tour in Chicago

  • 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
Gangsters and Ghosts Tour in Chicago
From USD 27.00
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  • Overview
  • What to Expect
  • Important Information
  • Reviews
  • Q&A
Select Date and Travellers
8pm TourMost Popular
Tour departs at 8pm
From USD 27.00
4pm Tour
Tour departs at 4pm
From USD 27.00
1pm Tour
Tour Departs at 1pm
From USD 27.00
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.
What to Expect
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.

Reviews (57)
1 - 5 of 47 reviews
Reviewed 1 week ago
Fantastic Tour!

The tour is sooo good. Even living in the suburbs of Chicago for 20 years I learned so much about Al Capone, The Chicago Fire and all the hauntings! Well worth your time and money!

Thank DHoffman60210
Reviewed 2 weeks ago
Nice tour

We found it interesting. Lots a good history. We saw a few places. I was just expecting a little bit more. Overall I’d give it an A-.

Thank markrom1967
Reviewed 4 weeks ago via mobile
Fun Time w/a historical lens on Chicago

Our tour guide was Stefan, he is very knowledgeable of the history of Chicago. We want out on a blustery Saturday night, though, the tour went quickly for the first hour, we went through the river walk, then headed down to the Palmer House Hotel,...More

1  Thank 669davew
Reviewed 4 weeks ago via mobile
Great Insight into Chicago Gangster History

Our guide, Davey, was incredibly knowledgeable about the gangster history of Chicago! He was also very personable and funny, but not in the cheesy way like you can get on some tours. ;) It was freezing and I was worried about being outside for 2...More

2  Thank AngieH0503
Reviewed 4 weeks ago
Very interesting and informative

Your guide takes you back to the days of Al Capone, the mob gagsters and bootleggers. He was very informative, interesting and fun as the bus drives you to some famous places of Chicago.

Thank dakotajude73
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Questions & Answers
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6 December 2018|
AnswerShow all 2 answers
Response from AngieH0503 | Reviewed this property |
We went in November. It was about 15 with the windchill. We were prepared and dressed appropriately. We enjoyed it. You do get to go inside a few times so that helps warm you up.
27 November 2018|
AnswerShow all 7 answers
Response from RJ S | Reviewed this property |
No, it ends at a different spot, but they give good directions on where you want to go after tour ends.
Sharon P
13 October 2018|
AnswerShow all 8 answers
Response from Theodore S | Reviewed this property |
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