Live the high life in Vince Vaughn’s former luxe Palmolive penthouse

The Palmolive Building, located in the heart of the Streeterville neighborhood, is a true Chicago landmark. It blends historic charm with modern elegance. The building was initially designed to house the headquarters of the Palmolive Company. Over the years, it has hosted some of Chicago’s most renowned residents and remains one of the city’s most sought-after addresses. Now, Vince Vaughn’s former penthouse is available for purchase, offering a rare opportunity to own a piece of Chicago’s architectural history in one of its most storied buildings.

The Palmolive Building is a prime example of Art Deco design, developed by Schmidt, Garden & Martin. It was the tallest building outside the Loop when it was completed, standing 37 stories tall. Its sleek, geometric design includes a striking setback, offering sweeping views of Lake Michigan and the skyline. Over time, the building evolved from a corporate headquarters to a mixed-use space, but its historical and architectural significance remains a defining feature of Chicago's skyline.

Dedicated in 1930, the Lindbergh Beacon was donated by the Sperry Gyroscope Company. It was mounted on the roof to honor Charles Lindbergh’s historic transatlantic flight. One of Chicago’s first of its kind, the beacon safely guided planes to the municipal airport, now Midway, with its powerful light. During World War II, the beacon was turned off as a safety precaution in case the enemy chose to launch an attack on Chicago. The beacon remained a prominent feature until 1981, when, due to the number of complaints of the light shining into the neighboring buildings, the beacon was taken down and is on display at the EAA Aviation Museum in Oshkosh, Wis. A refurbished World War II-era beacon is now lit on special occasions over a smaller arc than the original. 

In 1965, Playboy Enterprises purchased the Palmolive Building as its new headquarters. The upper floors were transformed into lavish clubhouses and business offices, and the penthouse was famously outfitted as a private residence for Hefner himself. This time, the building lit the sky with nine-foot letters spelling out PLAYBOY. The company remained in the Palmolive Building until 1989, after which it moved to new offices, and the building once again was re-purchased by Palmolive.

Granted Chicago and Federal Landmark status in 2001 and 2003, the Palmolive Building was sold to Draper and Kramer developers, who transformed it into a primarily residential building. The first two floors are dedicated to upscale offices and retail space. Uniquely, the building has separate business and residential addresses: 919 N. Michigan Ave. for commercial spaces and 159 E. Walton St. for residential units.

What was once Hugh Hefner’s and then Vince Vaughn’s luxury penthouse is now on the market again for $8.9 million. According to the listing agent, this one-of-a-kind duplex spans the 35th and 36th floors, offering 7,880 square feet of living space, including four bedrooms and four-and-a-half bathrooms. The home features breathtaking views of the Chicago skyline and Lake Michigan while providing modern amenities like a chef’s kitchen, a temperature-controlled wine room, and private elevator access.

With its rich past and modern luxuries, this penthouse offers an unparalleled living experience in one of the city’s most iconic buildings. It's not just a home, but a piece of Chicago’s legacy, where history and luxury come together in perfect harmony.