Chicago
The ratification of the 18th amendment to the Constitution in 1919 made the production and sale (including exportation) of alcoholic beverages illegal in the United States. This ushered in the beginning of what is known as the Gangster Era, a time that roughly spans from 1919 until 1933 when Prohibition was repealed. The 1920s saw gangsters, including Al Capone, Dion O'Banion, Bugs Moran and Tony Accardo battle law enforcement and each other on the streets of Chicago during the Prohibition era. Chicago was the location of the infamous St. Valentine's Day Massacre in 1929, when Al Capone sent men to gun down members of a rival gang, North Side, led by Bugs Moran.
Prohibition
After several years, prohibition failed in North America and elsewhere. Rum-running or bootlegging became widespread, and organized crime took control of the distribution of alcohol. Distilleries and breweries in Canada, Mexico and the Caribbean flourished as their products were either consumed by visiting Americans or illegally exported to the United States. Chicago became notorious as a haven for prohibition dodgers during the time known as the Roaring Twenties. Prohibition generally came to an end in the late 1920s or early 1930s in most of North America and Europe, although a few locations continued prohibition for many more years.