Chicago Mobsters and Haunted Mysteries Tour

50+ booked
The Congress Plaza Hotel & Convention Center: 520 S Michigan Ave, Chicago, IL 60605, USA
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  • Explore the beloved haunts frequented by Chicago’s notorious gangland figures of yesteryear
  • Stroll through the labyrinthine streets and shadowy alleyways, once bustling with illicit dealings
  • Listen to the eerie tale of the hitchhiking flapper girl, said to roam the beginnings of the legendary Route 66
  • Sense the lingering presence of departed spirits atop the remnants of the Great Chicago Fire
  • Discover the unsettling truth behind mobsters' utilization of Lake Michigan and their chosen dumping grounds

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Join-In Walking Tour

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From € 32.29

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What to expect

Embark on a family-friendly guided tour of Chicago, delving into the city's eerie tales of ghosts and gangsters. With your historian guide leading the way, venture through the Chicago South Loop district, once notorious for its vice activities during the 1920s and 30s.

Meet your guide in the heart of the South Loop, now a refined area that was once rife with underground speakeasies and bootleggers. Hear gripping accounts of Chicago's tumultuous past, including stories of infamous gangsters like Al Capone.

Explore the haunts where these figures once roamed, including former gangster hangouts, while enjoying a brief stop at a renowned hotspot. Uncover chilling ghost legends along the Chicago Riverwalk and Death Alley, visiting spooky sites like Palmer House and the Chicago Theatre.

Conclude your tour at the Congress Hotel, a reputedly haunted landmark, for a spine-tingling finish to your Chicago adventure

Meet your knowledgeable guide outside the Congress Hotel to begin your adventure
Meet your knowledgeable guide outside the Congress Hotel to begin your adventure
Traverse dark alleys and hidden corners where sinister secrets lurk
Traverse dark alleys and hidden corners where sinister secrets lurk
Wander along the Chicago riverside, hearing tales and mysteries of the city's past
Wander along the Chicago riverside, hearing tales and mysteries of the city's past
Marvel at the majestic Buckingham Fountain in Chicago while uncovering its haunted mysteries
Marvel at the majestic Buckingham Fountain in Chicago while uncovering its haunted mysteries
Explore the notorious Marshall Field and Company Building, steeped in mobster history
Explore the notorious Marshall Field and Company Building, steeped in mobster history
Learn about the sinister world of mobsters and the haunted mysteries that haunt Chicago's streets
Learn about the sinister world of mobsters and the haunted mysteries that haunt Chicago's streets

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