Actor Vince Vaughn's Chicago penthouse – once owned by Playboy's Hugh Hefner – is on the market for $13.9 million, according to TopTenRealEstateDeals.com. The 12,000-square-foot home, located in the Palmolive Building near Lake Michigan, has three floors and features a media room, billiards, a game room, a full bar and multiple terraces with views of the lake and city. Hefner's original office is on the top floor. For more information, visit TopTenRealEstateDeals.com.