In 1959, the building was acquired by Hugh Hefner. The mansion's basement, Hefner's original "grotto", had a swimming pool with a glass wall and attached bar. In addition to a game room and bowling alley, the residence contained a two-floor dormitory for Bunnies employed at the Chicago Playboy Club and discrete apartments that were occupied by several employees, including longtime Hefner aide Bobbie Arnstein.
For a period in the 1970s, Hefner divided his time between Chicago and the "Playboy Mansion West" in Los Angeles. The Chicago mansion boasted a brass plate on the door with the Latin inscription Si Non Oscillas, Noli Tintinnare ("If you don't swing, don't ring").
Although Playboy Enterprises remained headquartered in Chicago until 2012, Hefner left the city permanently for Los Angeles in 1974 following the conviction and ensuing suicide of Bobbie Arnstein, the culmination of an "investigation of drug use in Hefner's mansion" by U.S. Attorney for the Northern District of Illinois (and future Governor of Illinois) James R. Thompson. Derick Daniels (who served as president and chief operating officer of Playboy Enterprises from 1976 to 1982) resided in an apartment at the mansion during his tenure with the company. Eventually, the property was turned into a dormitory for the School of the Art Institute of Chicago, with Hefner formally deeding the building to the Art Institute in 1989. In 1993, the Chicago mansion was sold to developer Bruce Abrams and converted into seven high-price luxury condos. In 2011, one 7,874 sq ft (731.5 m2) condominium was placed for sale at an asking price of $6.7 million.