The sexual revolution partied hearty for 15 years in the basement ‘grotto’ of this 1899 mansion. Playboy founder Hugh Hefner bought it in 1959 and hung a brass plate over the door warning Si Non Oscillas, Noli Tintinnare (Latin for ‘If You Don’t Swing, Don’t Ring’). In the mid-1970s, Hef decamped to LA, and the building now comprises ultraluxury condos – but stopping by for a selfie still allows you to boast 'I've been to the Playboy Mansion.'
Playboy Enterprises stayed headquartered in Chicago until 2012, and then it too moved west. The last vestige is ‘Honorary Hugh M Hefner Way,’ which is what the city renamed Walton St (at Michigan Ave) in an official tip of the hat to Hef.
