10. Al Capone used to murder people in a brothel basement at 2222 S Wabash
With a speakeasy, brothel, and gambling den, the mob headquarters at The Four Deuces was a one-stop shop for debauchery. That was, of course, as long as you weren’t on Al Capone’s bad side, in which case he had a lavish meal prepared for you before you were brought into the basement, beaten all night, and murdered. The racket at the Four Deuces became too unwieldy under reformer William Dever so Capone fled to Cicero, and today only an open field remains in the bar’s place at 2222 S Wabash.