Playboy Retro: Chicago Girls

By Staff

<p><i>Playboy </i>began 60 years ago in Chicago, so it’s fitting we take a look back at the sexy photos of classic Windy City Playmates.<br></p>

Why is Chicago nicknamed the Windy City? Some claim it’s because of the gusty Midwestern weather; others say it’s a reference to the city’s windbag politicians. Perhaps it’s named for the wind of lustful sighs emitting from the mouths of the young men taking in the gorgeous Chicago women. Playboy began 60 years ago in Chicago, so it’s fitting we take a look back at some of the classic Windy City Playmates.

Born and raised in Chicago, Avis Kimble, with her sweet face, dirty blonde hair, lithe body and 39D bust, was a natural to appear in Chi-Town’s most famous magazine. This free-spirited babe lit up Playboy’s centerfold as Miss November 1962 and her pictorial captures both Avis’ luminous looks and her bohemian vibe. She was an art student when she posed for Playboy and our photos of Avis are beautiful enough to hang on the walls of any museum.


Jennifer Jackson worked as a Chicago Playboy Club Bunny while also attending college and pursuing modeling gigs. A busy woman for sure, but fortunately for us she had time to pose as March 1965’s Playmate of the Month. One glance at the delectable Jennifer and you think, “Here’s a woman so sexy and alluring, there’s no one else like her.” Which is true to a point. Her only match is her twin sister Janis, who Playboy shot alongside Jennifer for our 1964 Bunnies of Chicago feature.

Patti Reynolds was another luminous Chicago Bunny of the 1960s, but she left the club after saving up enough money to buy a horse. Patti was no racetrack degenerate but an enchanting equestrian who started her own career entering her thoroughbred, Frankie, in upscale horse competitions. Playboy was able to get this sultry raven-haired dream away from the stables to star as Miss September 1965. We didn’t get any photos of Frankie, but we believe these breathtaking shots of Patti will do you just fine.

Chicago is one of America’s great cities, and you’ll see the best of what the town has to offer in the gallery above.


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