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Al Capone’s Chicago: the sites and the story
Short answer: Al Capone ran the Chicago Outfit through Prohibition (roughly 1925–1931), making millions from bootlegging, gambling and vice. His Chicago is mapped on a gangster tour: old headquarters, the speakeasies, and the site of the St. Valentine’s Day Massacre. He was finally jailed in 1931 — for tax evasion, not the violence.
Who was Al Capone?
Brooklyn-born Alphonse Capone moved to Chicago in 1920 and rose to lead the Outfit by 1925, aged just 26. At his peak he controlled much of the city’s illegal liquor, gambling and protection rackets, hidden behind a public image of charity and cigars. The violence — including the 1929 massacre — eventually made him too notorious to ignore.
The sites a tour points out
- The Lexington Hotel — Capone’s former HQ (since demolished).
- The Green Mill — the Uptown jazz club and one-time speakeasy tied to the Outfit, still open.
- 2122 N Clark Street — the St. Valentine’s Day Massacre site (the garage is gone).
- Holy Name Cathedral — near where rival gangster Hymie Weiss was gunned down.
How it ended
The feds couldn’t pin the murders on him, so they got him for tax evasion in 1931. Capone served time including a stint on Alcatraz, was released in 1939 in failing health, and died in 1947. A gangster tour walks you through where it all happened.
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