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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 (64)
1 - 5 of 54 reviews
Reviewed 1 week ago
Fun, and we learned so much!

Gangsters and Ghosts exceeded our expectations. Our guide, Davy, was a wealth of knowledge and he found a way to make the tour fun for both the grownups and the kids.

Date of experience: January 2019
Thank Thomas M
Reviewed 1 week ago
Fantastic Tour!

This was a fun and informative tour. After a couple days in Chicago we were looking for something different and this fit the bill. Make sure you wear your walking shoes and appropriate clothes for outside. The tour guide did a great job and showed...More

Date of experience: October 2018
Thank 359jodieb
Reviewed 2 weeks ago
Informative, fun, even my teenagers enjoyed it!

This was a fun walking tour! It was just long enough without getting too exhausting. We learned about ghosts stories surrounding tragic deaths in Chicago, famous murderers, as well as gangsters. The walking was very doable and the break in the middle, at the Palmer...More

Date of experience: January 2019
1  Thank 470johannab
Reviewed 2 weeks ago
Fascinating Tour

Very interesting walk through Chicago's rich history! I can warmly recommend it and you will definitely love it! Price-performance ratio is second to none!

Date of experience: November 2018
Thank Guenthy
Reviewed 3 weeks ago via mobile
Fantastic tour

Put on your walking shoes and get ready to explore the darker side of historic Chicago. We highly recommend this tour. It was fantastic. Great views and sights of the city. Beautiful 50 degree night in December!! Thank you to our guide Stefan!

Thank 407kristeny
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Questions & Answers
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Marla K
2 January 2019|
AnswerShow all 3 answers
Response from dakotajude73 | Reviewed this property |
Call to ask them! I was with a bus tour that makes all of the arrangements.
5 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 Doodles45 | Reviewed this property |
The tour ended in the Congress Hotel not too far from the Art Institute. The hotel has a nice bar if you are in need of a drink after the tour.
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