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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 US$ 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 US$ 27.00
4pm Tour
Tour departs at 4pm
From US$ 27.00
1pm Tour
Tour Departs at 1pm
From US$ 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 (54)
1 - 5 of 45 reviews
Reviewed 4 days 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

Thank 669davew
Reviewed 6 days 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 6 days 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
Reviewed 1 week ago
Interesting and informative

Really enjoyed this tour. Our guide, Davey (as in Crockett so he said) was very charming and easy going. We were taken around places we would never have found on our own and I enjoyed the stories of old Chicago. The Palmer Hotel was a...More

1  Thank cathytrudgill
Reviewed 1 week ago via mobile
Must do!

We went last night and were blown away. Stefan was a great tour guide and you should definitely go at night. It is quite long and a lot of walking but so cool. Highly recommend!!

1  Thank imtrisholsen
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Questions & Answers
Ask a question
Sharon P
12 October 2018|
AnswerShow all 8 answers
Response from Bill K | Reviewed this property |
The tour includes going inside two hotels. The other locations you stand outside and the guide explains what went on- Pictures are allowed at all locations
Lark R
27 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...
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