The girls and Hef travel to Chicago to do more publicity for the girls' Playboy cover feature and to see Hef's hometown. Along with Hef's brother Keith, they visit Hef's old neighborhood, the elementary school he attended, and the house where Hef and Keith grew up. They visit Playboy headquarters and drop in on Monica Leigh's Cyber Girl photo shoot. That night, they go to dinner at Japonais restaurant, where they notice a group of four women at a nearby table checking out Hef. The next day, the girls get up early to appear on the Mancow radio show to be interviewed and to read the headlines. Later, Hef and the girls continue their tour of the city, during which Hef shows them the original Playboy Mansion. That night, a nightclub hosts a party for the group, and Holly notices that the same group of four women are there as well. The girls are all enthusiastic about Chicago and seeing Hef's old homes and haunts. Meanwhile, back at the Mansion in Los Angeles, Hef's absence makes it ...