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 featuring Cyber-Girl Monica Leigh! Sampling Chicago's nightlife, Hef, Keith and the girls dine at trendy eatery Japonais and then spend the morning with Chicago's famed shock jock, Mancow, reading the daily news for his morning radio show. After another evening out, everyone rides the wind (okay, a private jet) back to L.A. for some much needed relaxation.