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3.
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.
by C. P. Newman October 03, 2006
 
1.
an absolutely amazingly beautiful girl from Chicago. very Classy
Ya that new girl I've been dating is so amazing, TOTAL Chicago Girl
by fsdhjgs July 11, 2011
 
2.
When you are notorious for sucking bodybuilding cock, trolling gyms in hopes of being noticed and looking for attention from men on bodybuilding forums.

It can also mean someone who considers themselves getting ready for a show, but is always fat.

Example 1. Random bodybuilder finds a piece of ass at a gym or on a forum, he can say I scored me a chicagogirl aka. Erin, no matter the girls name or location.

Example 2. A girl is fat , eating on her treadmill and says she is prepping for the next show. You can say, hey, look at that chicagogirl prep over there.
Chicagogirl can be located at MD forums or RX. Probably a ton of others when looking for a bull fix. Very visible close to showtime.
by IronAsylum July 03, 2010