Gangland Chicago - The Historical Allure Of The 1920s


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Chicago's gangster history has fascinated world historians and visitors to the city in equal measure since the 1920s. The trauma of gangland Chicago during the legendary Prohibition decade has been immortalised in a variety of Hollywood movies - thrillingly represented in Brian de Palma's ‘The Untouchables’ and uproariously spoofed in Billy Wilder's ‘Some Like It Hot’. But what is it about this decade in Chicago's history that never fails to capture the national imagination?

For many, the figure of gang lord Al Capone is a large part of the allure. During the prohibition years of the 1920s, when the consumption of alcohol was banned in the United States, Capone effectively ran Chicago as his own town and went on to become the most notorious American criminal of the twentieth century. Over the course of the decade, Capone ran his empire from the Lexington Hotel at 22nd and Michigan Avenues in Chicago and profited from the extensive bootlegging racket that permeated the city. The illicit trade in alcohol, and the huge number of speakeasies (establishments used for the covert selling and drinking of alcohol) that sprang up around the city, played an enormous part in the success of Al Capone's nefarious gangs.

What's more, the iconic St Valentine's Day Massacre in 1929 - now seen as one of Chicago's most defining moments of the 1920s - has also ingrained itself in the American psyche. This famous incident in Chicago's history saw the shooting of seven people - six of which were gangsters - in the climax of a hefty rivalry between the city's two main gangs: Al Capone's South Side gang and Bugs Moran's North Side cronies.

Ultimately, Al Capone's arrest in 1931 for tax evasion led to his downfall, and this is seen by many as an ironic - and somewhat deflating - end to this nefarious gang leader. Essentially, the all-pervasive element of Chicago's gang warfare during the prohibition years is what makes it so appealing to history buffs - the amazing fact that one man could have had such complete criminal control over one city, and yet be brought down by such a mundane offence.

Of course, the eventual repeal of the prohibition act in 1933 was seen by many as a signal that the first great domestic experiment of the twentieth century had failed; a factor that further pushed Al Capone and his bootlegging gangs into legendary status. Today, many visitors to Chicago are keen to survey the city's gangland past and discover where old speakeasies were located, and this is relatively easy to do. Simply find a hotel in Chicago to use as your base and explore the old site of the Lexington Hotel, along with Capone's range of infamous haunts. And while this may appear to be a somewhat macabre vacation theme, it's nonetheless one that will provide a thrill for anyone who finds a bit of gory American history entertaining.

Andrew Regan is an online, freelance journalist.


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