Any kind of deteriorated vehicle, usually the kind that mom and dad make you drive in high school. Popular shitwagons include the Chevette, Pinto, Yugo, Festiva, etc.
"You got a car, dude?"
"Yeah, but it's a real shitwagon."
A car in piss poor condition that not even a hobo would sleep in. Usually smells like the county landfill from it's previous owners' offspring spilling soda and crapping their pants in the backseats. Called a shitwagon because of it's similarity to what a farmer hauls fertilizer in.
(n.) The physical embodiment of raw suckage. When something is so completely crappy that no other words can describe it. The complete opposite of Shit Kicker.
Cold, grey murder capital of the midwest. Life is so bad in Shitcago that the Cubs seem like a good baseball team to watch! Home of really bad haircuts.
Look, Shitcago is on fire again. Oh well, it's probably for the best.