Continue walking south on State Parkway until you reach #1340 (west side of street). Built in 1899 by architect James Gamble Rogers for George Snow Isham, a wealthy Chicago surgeon, this (originally) 72-room stately structure was purchased by Hugh Hefner in 1959 for $400,000. It became the original Playboy Mansion, home to Mr. Hefner and his iconic bunnies during the 1960s and 70s. Mr. Hefner added a pool, steam room, sauna, bowling alley, full size movie screening room and a 100-inch in diameter circular bed. (His bedroom doubled as his office!)

In 1971, Mr. Hefner purchased his Los Angeles mansion and began spending less time in Chicago. He eventually leased this mansion to the School of the Art Institute of Chicago in 1984 for $10 a year. The building was named Hefner Hall and served as a dormitory through 1990. Hefner later donated the mansion to the Art Institute, which sold it to a developer in 1993. The mansion was then converted into the luxury condominiums you see today.

When you're done imagining the legendary Playboy parties which happened here, continue walking south on State to Division Street. You've now seen the "heart" of the Gold Coast.

If you'd like to see more of the Gold Coast, proceed south on State Street. Otherwise, to reach the CTA Red Line Clark/Division stop, head west on Division Street. Once in the subway, take a southbound 95th/Dan Ryan train to return to the Loop.