The actual original Playboy mansion Chicago wasn't some sprawling West Coast estate with a grotto and a zoo. It was a massive, slightly imposing French Renaissance-style brick building on the Gold Coast. 1340 North State Parkway. If you walked past it today, you’d see a high-end condo building, but back in the late fifties and sixties, it was basically the center of the cultural universe. People forget that Hugh Hefner didn't start in Los Angeles. He was a Chicago guy through and through, and this house was his fortress.
It was a statement.
Hefner bought the 70-room palatial residence in 1959. At the time, the neighborhood was prestigious but quiet, definitely not prepared for a guy who worked in silk pajamas and kept a rotating door of celebrities in his basement. This wasn't just a house; it was a laboratory for a specific kind of mid-century masculinity that would eventually change how Americans thought about sex, work, and urban living.
The Basement Pool and the Underwater View
Everyone talks about the pool. It’s the legend. Honestly, the engineering of it was kinda wild for the time. Located in the basement, the pool featured a glass wall that looked into the "Bunny Hutch"—the dormitory where the Bunnies lived. If you were hanging out in the bar area, you could literally watch people swimming underwater. It sounds like a movie set, but it was very real and very expensive to maintain.
The house was built in 1899 for a guy named George Isham, a prominent surgeon. It’s funny to think about a Victorian-era doctor walking those halls before they were covered in thick shag carpeting and brass fixtures. When Hefner took over, he didn't just move in; he gutted the vibe. He installed a brass plate on the front door that famously read, SI NON OSCILLAS, NOLI TINNTINARE.
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Basically? "If you don't swing, don't ring."
The Famous Circular Bed
Then there was the bedroom. Hefner’s private quarters were legendary for being the place where he actually did most of his work. He was a notorious workaholic. He had this massive, eight-foot-wide circular bed that actually rotated. It wasn't just for show; it had built-in electronics, a desk, and a phone system so he could run the Playboy empire without ever having to put on a pair of pants.
He’d spend days in that bed.
He’d eat his meals there—usually fried chicken or crackers and jelly—and edit the magazine with a grease pencil. The room had no windows. Hefner famously hated the sun and preferred a perpetual midnight vibe. It allowed him to lose track of time, which is probably how you end up building a multi-million dollar media brand from your mattress.
Why the Original Playboy Mansion Chicago Was Different From LA
When people think of the Mansion, they usually picture the Holmby Hills estate in California. That place was airy, outdoor-focused, and felt like a resort. The original Playboy mansion Chicago was different. It was dark. It was moody. It felt like a private club because, well, it kind of was.
- The Chicago house was much more integrated into the city's social fabric.
- It served as the literal headquarters for the magazine’s staff before the Palmolive Building took over that role.
- The guest list was a weird mix of intellectuals and entertainers. You’d have Shel Silverstein hanging out in one corner and a jazz legend like Miles Davis in another.
The Chicago weather also played a part in the house's atmosphere. Because it was freezing for half the year, the party stayed inside. It was dense. The air was probably 40% cigarette smoke and 60% expensive cologne.
Life Inside the 1340 North State Dorms
A lot of people don't realize that the Mansion was also a dorm. The upper floors housed the women who worked at the Chicago Playboy Club. It was actually a pretty regulated environment. There were curfews. There were house mothers. It wasn't the free-for-all that the media liked to portray, though obviously, the parties were intense.
Hefner was obsessed with detail. He had a kitchen that ran 24/7. If a guest wanted a steak at 4:00 AM, they got a steak. This level of service was unheard of for a private residence at the time. He was essentially running a five-star hotel where the only way to get a room was to be famous or interesting enough to catch his eye.
The Downfall and the Move to California
By the early 1970s, things started to shift. The political climate in Chicago was getting complicated, and Hefner was facing increasing scrutiny from the local authorities. Plus, the center of the entertainment world was firmly in Los Angeles. Chicago was too cold, too restrictive, and maybe a little too small for the vision he had for the next decade.
He started spending more time in California.
In 1974, he officially moved his primary residence to the West Coast. For a while, the Chicago building was used by the Art Institute of Chicago as a dormitory, which is a hilarious twist of fate. Imagine being a freshman art student moving into a room that used to be a Playboy Bunny suite. The "swinging" history was painted over with beige dorm paint, but the bones of the house remained.
The Conversion to Condos
Eventually, the building was sold and converted into luxury condominiums. It’s now one of the most expensive addresses in the city. They kept the exterior facade—it’s protected because of its historical significance—but the interior is totally different. The rotating bed is gone. The underwater viewing window is gone.
If you have a few million dollars, you can buy a piece of it today, but it’ll feel like a modern, high-ceilinged Chicago apartment, not a 1960s bachelor pad.
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Researching the Legacy of 1340 North State
If you’re interested in the architectural history of the original Playboy mansion Chicago, you have to look into the work of George Isham and the early 20th-century Chicago elite. The house represents a bridge between the Gilded Age and the Sexual Revolution. It’s one of the few buildings in the city that saw both the height of Victorian formality and the absolute peak of counterculture decadence.
Architectural historians often point to the house as a prime example of how urban mansions were repurposed during the mid-century period. While many of its neighbors were being torn down for high-rise apartments, the Mansion survived because Hefner saw the value in its grand, imposing scale.
- Visit the neighborhood: Walking North State Parkway gives you a sense of the scale. Even without the brass plaque, the building stands out.
- Check the archives: The Chicago History Museum holds photos of the interior during the Playboy years that show the heavy velvet and wood paneling.
- Understand the shift: Compare the layout of the Chicago house with the Los Angeles floor plans to see how Hefner's philosophy on "the good life" evolved from an urban club feel to a sprawling estate.
Practical Steps for History Buffs
If you want to dive deeper into the reality of the Chicago years, stop looking at the tabloids and start looking at the business records. The Chicago mansion was where the business of Playboy was perfected.
First, look for the book The Playboy Mansion by Victor Lownes, who was a key figure in the early days. He gives a much more grounded perspective on the logistics of the house. Second, look up the local Chicago zoning battles from the sixties. It’s fascinating to see how the "moral" objections of the neighbors were actually handled in court.
Finally, if you’re ever in Chicago, take a walk through the Gold Coast. The building is located at the corner of State and Schiller. It’s private property now, so don't try to go inside, but standing on the sidewalk gives you a real sense of why Hefner chose it. It was big, it was bold, and it looked exactly like the kind of place a man who wanted to change the world would live.
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The house at 1340 North State Parkway remains a monument to a specific era of American history. It wasn't just about the parties; it was about the collision of old-world Chicago wealth and new-world media influence. It was the place where the "Playboy" brand was born, and even though the party moved West, the soul of that era is still baked into the brickwork of the Gold Coast.