Original Playboy Mansion

Notable Building in Gold Coast

Image by Raymond Boyd Getty Images

The sexual revolution started in the basement ‘grotto’ of this 1899 manor. Hugh Hefner bought the mansion in 1959 and hung a brass plate over the door warning ‘If You Don’t Swing, Don’t Ring.’ Heavy partying ensued. In the mid-1970s, Hef decamped to LA. The building contains condos now, but a visit still allows you to boast 'I've been to the Playboy Mansion.'

Hef's company, 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.