2 definitions by Supajew

chicago up

The Obama snow-day policy equivalent of "man up." To make all schools in the country as hardcore about not having snow days as the schools in Chicago are. Derived from the comment Barack Obama made about how his daughters' school was cancelled "because of what? a little ice?"

"Dude, there's like 3 inches of snow and we don't have school! What the hell is this?"
"Yeah i know man, our school really needs to Chicago up"

by Supajew January 29, 2009

cumboys

A homosexual squad where you do homosexual things to each other

You see those Cumboys?
Yea, I'm looking at the black one
Same

by Supajew December 29, 2016