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S1:E13 My Kind of Town
First Aired: November 20, 2005
Hef, Holly, Bridget and Kendra blow into the Windy City, Hef's birthplace and home of Playboy Enterprises, Inc., to continue promoting the November issue of Playboy. They take in a visit to Playboy HQ, dine at trendy eatery Japonais and more!
