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Constructed in 1899 by architect James Gamble Rogers for the surgeon George Snow Isham and his wife Katharine, this French Renaissance Revival style 72-room mansion once stood as a symbol of wealth in the prominent Gold Coast neighborhood. In their home, the Ishams hosted such individuals as Theodore Roosevelt and Admiral Robert Peary. Then in 1959, Hugh Hefner purchased the estate for $400,000; and for the next twenty years, this home served as the first Playboy Mansion. Hefner eventually leased the mansion to the School of Art Institute in Chicago in 1984, then donating it in 1991. The Art Institute sold the house to a developer in 1993 who converted it to luxury apartments.


  • House facade
  • Hugh Hefner and the pool once located in the house's basement

In 1899 James Gamble Rogers, noted for his collegiate architectural designs at such schools as Yale and Columbia, constructed a grand mansion in the Gold Coast neighborhood of Chicago for the prominent surgeon George Snow Isham and his wife Katharine. This French Renaissance Revival style 72-room mansion once hosted such individuals as Theodore Roosevelt and Admiral Robert Peary. 

Then in 1959, Hugh Hefner purchased the estate for $400,000 with the intent on converting it into his residence and headquarters of his new publication, Playboy Magazine. For the next twenty years, this home served as the Playboy Mansion and infamous party house. Henfer made some major alterations to the building, such as installing a bowling alley, game room, a dormitory for the Bunnies, and a pool in the basement. Hefner also installed a brass plate over the front door with the Latin inscription Si Non Oscillas, Noli Tintinnare, "If you don't swing, don't ring.”

In the early 1970s, Hugh purchased an estate in Los Angeles and began splitting his time between the two cities. He left Chicago permanently in 1974 after the suicide of his personal assistant Bobbie Arnstein. Hugh Hefner eventually leased the mansion to the School of Art Institute in Chicago in 1984, then donating it in 1991. The Art Institute sold the house to a developer in 1993 who converted it to luxury apartments.

Move into the Original Playboy Mansion — for $3.7 Million. Chicago Magazine. October 18, 2018. October 30, 2018. http://www.chicagomag.com/Chicago-Magazine/November-2018/Move-into-the-Original-Playboy-Mansion--for-37-Million/#/0.

Spula, Ian. Live at the Old Playboy Mansion—For $3 Million. Chicago Magazine. September 5, 2014. October 30, 2018. https://www.chicagomag.com/real-estate/September-2014/Get-in-on-the-Ground-Level-at-the-Old-Playboy-Mansion-For-2995-Million/.

Buy your own piece of the original Playboy Mansion for as little as $2.5M. The Real Deal. October 27, 2018. October 30, 2018. https://therealdeal.com/chicago/2018/10/27/buy-your-own-piece-of-the-original-playboy-mansion-for-as-little-as-2-5m/.

Rumore, Kori. Data: A Playboy's guide to Hugh Hefner's Chicago. Chicago Tribune. September 27, 2017. October 30, 2018. https://www.chicagotribune.com/news/ct-playboy-in-hefners-chicago-040516-htmlstory.html.