Prohibition Chicago: Myth vs. Reality Walking Tour

More than 100 years later, stories of Prohibition-era Chicago still capture the public’s imagination. But the portrayal of that era in popular culture isn't always accurate. On this tour, you’ll hear how the culture in turn-of-the-century Chicago helped bring about the 18th Amendment through stories of notorious vice districts along the Chicago River and the South Loop. We'll talk about the rise of Al Capone during the infamous “Beer Wars,” culminating in the St. Valentine’s Day Massacre. Along the way, we’ll talk about how the city played a role in the popular and artistic growth of jazz, and how Chicago during the Roaring Twenties has been depicted on screen, in blockbusters such as "The Untouchables" and "Chicago." Please be advised that this tour contains stories of murder and sex work. Although children are welcome on this tour, parents should use their discretion in determining whether it is suitable for those under 15.

1. 1

   Chicago Riverwalk

   30 min

   As we stroll the Riverwalk (or Wacker Dr., depending on crowds), we'll discuss the rise of vice districts and organized crime in Chicago, and how the city played a role in the fight to ratify the 19th Amendment, which ushered in the Prohibition Era.

2. 2

   Stop 2

   10 min

   Now a restaurant named after a beloved sportscaster, Harry Caray's Italian Steakhouse was where Frank Nitti, Al Capone's bodyguard and successor as head of the Chicago Outfit, lived for a while. We'll talk about how he's been portrayed in the movies hasn't always been accurate.

3. 3

   Stop 3

   5 min

   After crossing back into the Loop, we'll talk about the role Chicago played in the popular and artistic growth of jazz during the Roaring Twenties. We'll stop at the site of a now-demolished place where Capone and jazz intersected.

4. 4

   The Chicago Theatre

   10 min

   The Chicago Theatre was built in 1921 and its marquee is an icon of the city and featured in dozens of movies and TV shows set in the city. We'll talk about women that inspired the hit musical "Chicago" and its many iterations.

5. 5

   Palmer House Hilton Historic Lobby

   15 min

   A hotel whose history dates back to 1870, the Palmer House was renovated and expanded in the mid-1920s and remains an example of that era's wealth and elegance.

6. 6

   Chicago Cultural Center

   15 min

   Opened in 1897 as the city's first public library, the Chicago Cultural Center was used in two crucial scenes in "The Untouchables."

• Wheelchair accessible
• Infants and small children can ride in a pram or stroller
• Public transportation options are available nearby
• Transportation options are wheelchair accessible
• All areas and surfaces are wheelchair accessible
• Suitable for all physical fitness levels

For a full refund, cancel at least 24 hours before the scheduled departure time.