Former residence of Hugh Hefner—the founder of Playboy Magazine—this Original Playboy Mansion is famous for the legendary parties attended by iconic celebrities. Hef purchased the mansion in 1959 and lived and worked there until 1971. Now, Hef resides in California at the Playboy Mansion West and the original has been converted into private residences. However, the regal architecture can still be seen from the outside, prompting tourists to click pictures of this cultural marvel. 

Phone: (312) 567-8500

Cross Streets: Between E Banks St and E Schiller St/W Schiller St