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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
4pm Tour
Tour departs at 4pm
1pm Tour
Tour Departs at 1pm
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 (38)
1 - 5 of 34 reviews
Reviewed yesterday
Very educational

Not really a ghost tour, but did learn about some of the horrible accidents that occurred in Chicago's history that you never learned in school. Our hotel was in the same building that had the second largest building fire in the US that claimed 600+...More

Thank Manuel A
Reviewed yesterday
Very fun and entertaining

We took this tour with Davey and he was very fun to listen to obviously knew a great deal about Chicago's history. It was a nice 2 hours and it even ended at our hotel, which was a fun surprise.

Thank Ashley M
Reviewed 2 days ago
The pace was good. The narrative was interesting.

Our guide, Stephen, (I think I spelled his name wrong. He was a nice young man of Polish descent.) was very knowledgeable about the subject matter. There was a nice mix about the subject matter, gangsters and ghosts.

Thank Doodles45
Reviewed 1 week ago
Amazing Tour! Would recommend in a heart beat!

It was my husband and I's first time in Chicago and we decided to take this tour at night. It was definitely one of our highlights of the trip! I STRONGLY recommend this tour, especially at night. It was so much fun and so informative....More

Thank stephcharron9
Reviewed 1 week ago via mobile
Excellent walking tour

We took this tour last night. Guide was Lauren. She did a fantastic job. Informative, funny, enthusiastic. Highly recommend.

Thank Scooter1618
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Questions & Answers
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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
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...
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