The first-ever Playboy Mansion, acquired back in 1959 by Hugh Hefner, is still located in Chicago's exclusive Gold Coast neighborhood at 1340 North State Parkway.
The Chicago Playboy Mansion was a 70-room classical French brick-and-limestone, Victorian-style mansion built from 1899-1903 and designed by James Gamble Rogers as the primary residence for Chicago-area surgeon, Dr. George S. Isham.
Playboy founder Hugh Hefner turned the home into the first-ever Playboy mansion, using it primarily for parties and events from 1959 until the mid-1970s when he relocated to Los Angeles.
During the early '70s, Hefner lived in both the Chicago Playboy mansion and another Playboy Mansion called "Mansion West". (Mansion West was originally built in 1927 in the Gothic-Tudor style and is located at 10236 Charing Cross Road in the Holmby Hills area of Los Angeles.) Hefner later moved full time into the California mansion in 1974.
After Hefner decamped for L.A., Playboy Enterprises leased the Chicago mansion to the Art Institute of Chicago, which it used for student housing until the early '90s. (In 1989, Playboy donated the mansion to the Art Institute.)
Just like Hefner, who became burdened by runaway expenses associated with the upkeep and maintenance of the Holmby Hills mansion, the Art Institute found it financially prudent to sell the Chicago Mansion, which it did in 1993 to Chicago real-estate developer Bruce Abrams. (Abrams gutted the mansion and renovated it into seven separate units. As of 2011, only one unit in the building leads directly out to the property's garden and private patio. (The three-bedroom 3,900-square-foot condo still retains its beautiful architectural details like ornate moldings, built-in shelving and curved archways, and runs for a mere $2.9 million dollars as of 2011.)
As in the movie, the Chicago Playboy Mansion actually did have an embossed brass plate at the front gate above the doorbell with the Latin inscription, "Si Non Oscillas, Noli Tintinnare", which translates to "If you don't swing, don't ring". According to legend, Hefner's intention of using this shibboleth was to serve as an expedient way in determining which potential Playmates were products of a Classical education or not, as he found the combination of beauty and brains to be an aphrodisiac. See more
You're the only man I know who puts his hand up a girl's skirt looking for a dictionary.