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Mobsters & Haunted Mysteries of Chicago Walking Tour

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Highlights

  • Discover the dark side of Chicago on a haunted walking tour after dusk.
  • Visit America’s most notorious gangster’s favourite hangout location.
  • Hear ghostly stories of the hitchhiking flapper girl as you walk by the start of Route 66.
  • Walk through the Alley of Death and hear about its tragic history.

Overview

As the sun sets, learn about the dark past of the city with our gangsters and ghosts tour in Chicago. Led by an expert guide, walk through alleys, waterways, and the backstreets of the city as you uncover hidden secrets along the way.

This tour begins at the Congress Plaza Hotel, the most haunted location in the state of Illinois. Spend two hours walking around the city and learning about Chicago’s spine-tingling history. If you’re into true crime, murder mysteries, and spooky stories, then this tour is for you!

Hear harrowing tales of how mobsters once ruled the city and visit Al Capone’s favourite hangout place. See under the ‘L’ and learn about how it was once was a hotbed of crime. Make your way to Couch Place, also known as the Alley of Death. Hear about the tragic fire at the Iroquois Theatre – the beginning of the supernatural sightings at the Alley of Death. Walk by the Chicago River and reflect on the tragedy that took place on these waters in 1915.

This Chicago haunted tour is filled with the tales of the hitchhiking flapper girl, the departed souls from the Great Chicago Fire, and plenty more. Become immersed in the city’s fascinating history and if you’re lucky, you may even encounter a paranormal sighting along the way!

Inclusions

  • Guided walking tour in Chicago

Exclusions

  • Entry to attractions

Additional information

Monday – Thursday: 7pm
Fridays, Saturdays & Sunday: 4pm & 7pm
Meeting point: In front of the Congress Plaza Hotel & Convention Center – 520 S. Michigan Ave, Chicago, IL 60605
End point: Near N. Michigan Avenue and Wacker Drive
Please arrive at the meeting point at least 15 minutes prior to the scheduled tour time. Your guide will be wearing an orange hat that says, 'Experience First'.
This tour covers approximately 1.5 miles at a leisurely pace.
This tour is wheelchair accessible.
Our tours go on rain or shine. If we have to cancel due to severe weather conditions, you’ll get a full refund.
Free cancellation and amendments up to 48 hours before scheduled tour.
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Highlights

  • Discover the dark side of Chicago on a haunted walking tour after dusk.
  • Visit America’s most notorious gangster’s favourite hangout location.
  • Hear ghostly stories of the hitchhiking flapper girl as you walk by the start of Route 66.
  • Walk through the Alley of Death and hear about its tragic history.