Gangsters and Ghosts Tour in Chicago

  • Refundable
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Activity Highlights
This is a typical itinerary for this product

Stop At: The Loop, 701 S State St, Chicago, IL 60605-2108

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. The tour is about 1.5 miles long with frequents stops and a refreshment/restroom break.

Duration: 1 hour

Stop At: Millennium Park, 201 East Randolph Street, Chicago, IL 60601-6530

Home to Cloud Gate and a famous Chicago landmark.

Duration: 15 minutes

Stop At: Palmer House Hilton Historic Lobby, 17 E Monroe St, Chicago, IL 60603-5608

Stop for a break at the Palmer House Hotel, rumored to be haunted. The Palmer House Hotel is the oldest hotel in Chicago and considered the oldest continuously operating hotel in the USA.

Duration: 20 minutes

Stop At: Chicago Riverwalk, Chicago, IL 60601

You'll walk along the Riverwalk during the tour, which 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.

Duration: 15 minutes

Pass By: Cloud Gate, 201 E. Randolph St. Millenium Park, Chicago, IL 60601-6530

Will be seen on the tour - also known as "the bean!"

Stop At: The Chicago Theatre, 175 N State St, Chicago, IL 60601-3623

Stop for photos at this famous Chicago landmark!

Duration: 15 minutes

Stop At: The Congress Plaza Hotel & Convention Center, 520 S Michigan Ave, Chicago, IL 60605, USA

Tour ends at the Congress hotel, named one of the most haunted places in the State of Illinois. Al Capone set up his headquarters here, and his ghost is most frequently seen near his old suite on the 8th floor.

Duration: 15 minutes

Activity Details
Interested in exploring Chicago from the perspective of ghosts and gangsters? Want to really immerse yourself in the history of this great American city, right from the locations that started it all? This tour visits the locations frequented by some of Chicago's most notorious gangsters along with many of the most haunted locations in Chicago!

You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District! Tour departs from 71 E Wacker Drive.
Departure & Return
Departure Point71 E Wacker Dr, Chicago, IL 60601, USA
Return520 S Michigan Ave, Chicago, IL 60605, USA
What's Included
  • Walking tour of Chicago’s gangsters and ghost stories
  • Gratuities
  • Entry/Admission - The Chicago Theatre
Additional Information
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Near public transportation
  • Travelers should have a moderate physical fitness level
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This tour/activity will have a maximum of 10 travelers
  • Face masks required for guides in public areas
  • Social distancing enforced throughout experience
  • Regular temperature checks for staff
  • Contactless payments for gratuities and add-ons
  • This is a walking tour with limited group size to maintain social distancing.
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveler Reviews

Average based on 237 reviews.

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  • I’m born and raised in Chicago and didn’t know 90% of these stories/facts! Adam was a wonderful guide and kept it fun/moving!

  • Caleb was an amazing tour guide offering loads of Chicago fun facts and history- was a fun way to see the river walk and loop for our family of five!

  • Our guide was Kai and she was informative and patient with the group. This is a walking tour but there are lots of stops making it an easy manageable walk. The tour does not end where it started so plan on that. It was about a 20 minute walk back to the area of starting.

  • Kai was great. She has a great depth of knowledge about the area. She has an awesome energy. FYI, the tour has a good deal of walking...but not too much.

  • Loved this tour. Our tour guide Caleb was great! Very knowledgeable and kept everyone's attention. It was the perfect way to get some Chicago history and the perfect mix of gangsters and ghosts. HIGHLY RECOMMEND

  • Caleb was so informative and entertaining! It was the perfect balance of mafia and ghost stories. He presented each location’s back story with such flair that it made the whole experience fun.

  • So fun!! Olivia was great! Great night in the city! Loved learning about the city’s history and scary!

  • H.H. Holmes was my favorite. Learned so much about Capone. Can’t forget the Congress Hotel. Each experience is different because of the person telling the story, so worth going again and again.

  • Beautiful day. Great guide. Glad we did it! Learned a lot of creepy things about Chicago and some interesting history

  • My wife and I really enjoyed the tour. Conner was a great tour guide and we enjoyed learning about the history of Chicago. We would recommend the tour to anyone who wants to hear some interesting history related to gangsters and ghosts.

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237 reviews
$27 USD
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Adult(s) upto 9 passengers
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