Think You’re A Playboy worthy of Hef’s extravagant lifestyle? Well, now you can live like one. Part of Mr. Hefner’s original Playboy Mansion on Lakeshore Drive is for sale for a cool 2.9 million.
The 3 bedroom, 3.1 bath condo is the only unit in the building that leads out to the mansion’s private garden and includes a private patio so you can throw your own epic Mid-Summer’s Dream parties. Though Hef hasn’t resided in the Windy City since the ‘80s, the original Chicago mansion has seen it’s share of debauchery, silk pajamas and bunny ears.
The 48-room mansion is now a landmark and tourist attraction full of history and rich with glory and secrets in it’s walls. Designed by architect James Gamble Rogers in 1899, Hefner originally donated the house to the Art Institute of Chicago when he moved to Cali. In 1993, the building was gutted and divided into seven expensive condos, so the indoor swimming pool, the sealed living room trapdoor and brass plate over the door warning ‘If You Don’t Swing, Don’t Ring’ are gone forever.
Though the girls are not included in the asking price, Chicago does have more girl-next-door types than LA so you might just get lucky.
Your New Address:
1340 North State Parkway #1S
Chicago, IL 60611
Related Articles
Inside Louis Vuitton’s Soho Pop Up Celebrating 130 Years of the Monogram
Louis Vuitton opens a dedicated Soho pop up celebrating 130 years of the Monogram, featuring immersive rooms and iconic bags.
Jay Shetty on Silence, Loss, and the Power of Presence
Jay Shetty opens up about loss, rebellion, mindfulness, and why silence—not perfection—has become the guiding force behind his influence.
Haute Brand Alert: Brave Pudding’s Cashmere Sock Shoes Are The New It Footwear
Inside Brave Pudding: Sarah Fiszel on Hamptons Strolls sock shoes, luxury comfort, Trims, and effortless style.
The Haute List: The January Must-Haves For Haute Living Editors
The January 2026 Editor Haute List spotlights the most coveted luxury items, experiences, and trends curated by Haute Living editors.
Miami Based Celebrity Makeup Artist Carolina Banegas Shares Her Beauty Must Haves
Miami based celebrity makeup artist Carolina Banegas dishes on her favorite beauty tips and tricks,
What UK Interest Cuts Could Mean for Mortgages and Savings
Bank of England cuts base rate to 4.25%. Learn how it affects mortgages, first-time buyers, landlords, savings, and the UK economy.
Latest Stories
Trending Articles
Related Articles
Inside Louis Vuitton’s Soho Pop Up Celebrating 130 Years of the Monogram
Louis Vuitton opens a dedicated Soho pop up celebrating 130 years of the Monogram, featuring immersive rooms and iconic bags.
Jay Shetty on Silence, Loss, and the Power of Presence
Jay Shetty opens up about loss, rebellion, mindfulness, and why silence—not perfection—has become the guiding force behind his influence.
Haute Brand Alert: Brave Pudding’s Cashmere Sock Shoes Are The New It Footwear
Inside Brave Pudding: Sarah Fiszel on Hamptons Strolls sock shoes, luxury comfort, Trims, and effortless style.
The Haute List: The January Must-Haves For Haute Living Editors
The January 2026 Editor Haute List spotlights the most coveted luxury items, experiences, and trends curated by Haute Living editors.
Miami Based Celebrity Makeup Artist Carolina Banegas Shares Her Beauty Must Haves
Miami based celebrity makeup artist Carolina Banegas dishes on her favorite beauty tips and tricks,
What UK Interest Cuts Could Mean for Mortgages and Savings
Bank of England cuts base rate to 4.25%. Learn how it affects mortgages, first-time buyers, landlords, savings, and the UK economy.
Subscribe to Haute Living
Receive Our Magazine Directly at Your Doorstep
Embark on a journey of luxury and elegance with Haute Living magazine. Subscribe now and have every issue conveniently delivered to your home. Experience the pinnacle of lifestyle, culture, and sophistication through our pages.
Haute Black Membership
Your Gateway to Extraordinary Experiences
Join Haute Black and unlock access to the world's most prestigious luxury events