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the beginning of what is known as the Gangster Era, a time that roughly spans from 1919 until 1933 when Prohibition was repealed.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.
Overton Corners–Lacolle 221 Border Crossing
During the era of Prohibition in the United States, this crossing was one of the busiest on the US-Canada border. The roads leading to it in both the US and Canada were in good condition and was a popular route for traffic traveling between Montreal and New York City. During that era, it was common for large queues of southbound traffic to build up approaching US Customs, as people attempted to smuggle alcohol into the United States.