Prohibition Chicago: Myth vs. Reality Walking Tour
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Explore Chicago’s influential role in jazz during the Roaring Twenties
Experience iconic filming locations featured in The Untouchables
Discover stories behind the women who inspired Chicago musical
Explore the elegant architecture and history of Palmer House
Prohibition-Era Chicago: Crime, Jazz, and Hollywood
The tour begins at Pioneer Court, where Michigan Avenue meets the historic Tribune Tower and Apple Store. Here, guests will explore the arrival of the first non-Indigenous people to the region and discover how their presence contributed to Chicago’s transformation from a small settlement into a thriving metropolis. The journey continues to DuSable Bridge, a landmark famously featured in an early scene of *The Untouchables*, connecting Chicago’s history with its enduring presence on the silver screen.
Along the Chicago Riverwalk, or Wacker Drive when crowds require, the story turns to the city’s notorious vice districts, organized crime, and the social forces surrounding Prohibition. Guests will learn about Chicago’s connection to the fight for ratification of the 19th Amendment and the rise of the 18th Amendment. At Frank Nitti’s former residence, now home to Harry Caray’s Italian Steakhouse, the tour explores Nitti’s role as Al Capone’s bodyguard and eventual successor as head of the Chicago Outfit, while separating historical fact from Hollywood mythology.
Crossing back into the Loop, the tour examines Chicago’s important role in the popular and artistic development of jazz during the Roaring Twenties. Guests will visit locations connected to the intersection of jazz and Capone’s Chicago before continuing to the iconic Chicago Theatre. Built in 1921, its famous marquee has appeared in countless films and television productions. The tour also explores the women who inspired the hit musical *Chicago* and the many versions that followed.
The final stops reveal another side of 1920s Chicago, from the elegant Palmer House, whose history began in 1870, to the Chicago Cultural Center, originally opened in 1897 as the city’s first public library and later featured in two important scenes from *The Untouchables*. The tour concludes at the striking Carbide and Carbon Building, celebrated for its Art Deco architecture and a secret connected to the Prohibition era. More than a century later, Chicago’s stories of crime, jazz, ambition, and scandal continue to fascinate audiences, even as popular culture often reshapes the historical truth. Please note that the tour includes stories involving murder and sex work; children are welcome, but parental discretion is recommended for guests under 15.
Prohibition-Era Chicago: Crime, Jazz, and Hollywood
The tour begins at Pioneer Court, where Michigan Avenue meets the historic Tribune Tower and Apple Store. Here, guests will explore the arrival of the first non-Indigenous people to the region and discover how their presence contributed to Chicago’s transformation from a small settlement into a thriving metropolis. The journey continues to DuSable Bridge, a landmark famously featured in an early scene of *The Untouchables*, connecting Chicago’s history with its enduring presence on the silver screen.
Along the Chicago Riverwalk, or Wacker Drive when crowds require, the story turns to the city’s notorious vice districts, organized crime, and the social forces surrounding Prohibition. Guests will learn about Chicago’s connection to the fight for ratification of the 19th Amendment and the rise of the 18th Amendment. At Frank Nitti’s former residence, now home to Harry Caray’s Italian Steakhouse, the tour explores Nitti’s role as Al Capone’s bodyguard and eventual successor as head of the Chicago Outfit, while separating historical fact from Hollywood mythology.
Crossing back into the Loop, the tour examines Chicago’s important role in the popular and artistic development of jazz during the Roaring Twenties. Guests will visit locations connected to the intersection of jazz and Capone’s Chicago before continuing to the iconic Chicago Theatre. Built in 1921, its famous marquee has appeared in countless films and television productions. The tour also explores the women who inspired the hit musical *Chicago* and the many versions that followed.
The final stops reveal another side of 1920s Chicago, from the elegant Palmer House, whose history began in 1870, to the Chicago Cultural Center, originally opened in 1897 as the city’s first public library and later featured in two important scenes from *The Untouchables*. The tour concludes at the striking Carbide and Carbon Building, celebrated for its Art Deco architecture and a secret connected to the Prohibition era. More than a century later, Chicago’s stories of crime, jazz, ambition, and scandal continue to fascinate audiences, even as popular culture often reshapes the historical truth. Please note that the tour includes stories involving murder and sex work; children are welcome, but parental discretion is recommended for guests under 15.
- Entrance fee
- Gratuities
- Bottled water
$ 35
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Activity Provider: Chicago History Walking Tours