an absolutely amazingly beautiful girl from Chicago. very Classy
Ya that new girl I've been dating is so amazing, TOTAL Chicago Girl
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A woman exhibiting above-average attractiveness from the neck up, but who is unacceptably - and often surprisingly/disappointingly - overweight in the body. The term stems from Tucker Max's contention that Chicago's extremely short swimsuit season gives the otherwise attractive women there little incentive to exercise.
I met this chick online and saw her headshot and she was fine as hell. But when I finally saw a full-body shot she turned out to be a total Chicago Girl.
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