Chicago native Hugh Hefner opened the world's first Playboy Club on East Walton, in the Gold Coast, in February of 1960.

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"Keyholders" -- high roller VIPs -- could enter the club at any time to "indulge in music, alcohol, and nubile women." Newsweek referred to each of the 40 Playboy Clubs as a "Disneyland for adults."

The flagship club closed in 1986, with the last of all the clubs to close in 1991.