Hef, Holly, Bridget and Kendra blow into the Windy City, Hef's birthplace and home of Playboy Enterprises, Inc., to promote the November issue of Playboy. And what a trip it is! After a night's rest at the luxurious Peninsula Hotel, Hef and his brother Keith give the girls a guided tour of their childhood haunts, and they also take in a visit to Playboy HQ--where they walk in on a sexy photo shoot...