Historic Gangster Locations in Chicago
Step back in time and explore the Windy City through the lens of its fabled past. Chicago's streets echo with tales of notorious gangsters, legendary heists, and speakeasy secrets. Check out our map for a glimpse of our tour stops, both on and off the bus, and discover the sites that set the scene for the stories we tell. From Al Capone's old haunts to the notorious St. Valentine's Day Massacre site, dive into the heart of Chicago's thrilling gangster era.
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Water Tower Place is the first vertical mall in the United States and features famous retailers, restaurants and entertainment venues, including LEGO® Store, the flagship American Girl, Harry Caray’s 7th Inning Stretch and the Chicago Sports Museum, just to name a few.
Across the street from the Water Tower Place shopping mall on Chicago’s Magnificent Mile is the meeting spot and departure location for our Chicago Crime Tour and Night Crimes Tour! Arrive at least 15 minutes before your selected tour. Hop aboard a luxury climate-controlled coach bus and begin a 1.5-2 hour tour of Chicago crime history from the beginning of the 19th century through the modern era.
Bus pickup is OUTSIDE 163 E. Pearson St at the SE side of Michigan Ave and Pearson St. Meet us here!
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The Biograph Theater is a historic landmark building. John Dillinger, one of the world’s most famous bank robbers, walked his last steps outside of this theater. This infamous site is listed in the National Registry of Historic Places.
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The Prohibition-era battle between two powerful Chicago gangs -- the South Side gang aka The Outfit led by Al “Scarface” Capone and the North Side gang led by George “Bugs” Moran -- ended in one of the bloodiest crime scenes in Chicago mob history on February 14, 1929.
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The Jewelers Building at 35 E Wacker Dr is a historic landmark building that was home to Chicago Gangster Al Capone’s infamous speakeasy.
Carbide & Carbon Building was built during Prohibition. Learn the story behind the architecture and design choices for this significant addition to the Chicago skyline.
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This building was one of the residences of Frank “The Enforcer” Nitti, one of Al Capone’s lieutenant and successor. Go inside to see Nitti's Vault, a mob museum, and historic bootlegging tunnels.
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Many mob funerals were held at Holy Name Cathedral. North Side Gang headquarters was across the street at a florist. On a Chicago Crime Tour, your expert tour guide will provide an in-depth narration of the last moments of Chicago gangsters Dean O’Banion and Hymie Weiss at Holy Name Cathedral.
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Museum of Contemporary Art
The Magnificent Mile
John Hancock Building
North Avenue Beach
Oak Street Beach
Oz Park
Lincoln (Abraham) Park
Chicago Riverwalk
These are just some of the sights we see and stories we share on our tours! For the full scoop, you’ll have to join and find out for yourself!