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To have sex with no condom
"That chick was a whore, please tell me you did'nt go Chicago Bare"

"I did'nt even care I was out of condoms, she was so hot I just went Chicago Bare."

"You totally deserve the Drip for always going Chicago Bare like you do."

"Your wildin out, kissing girls in the mouth and Chicago Baring bitches."
by Michael and Ian Richards February 11, 2009