Original Playboy Mansion
Pretty self-explanatory - this used to be the Playboy Mansion. NOTE: this is someone's actual house so no entry
Before Hugh Hefner moved out to Vegas (it was Vegas, right? I probably should look this up) and made his massive Playboy Mansion, he actually lived in and used this Gold Coast residence as his original Playboy Mansion. Hefner is from Illinois, so it makes sense. Keep in mind that this building is still private property and owned/used by someone, so don't be a dumdum and annoy them.
1340 N State Pkwy, Chicago, IL 60610
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