Chicago--Uprise (Uriah, Maya, etc.), Character (Alan), Clemente, Burnham, Wilson--brought me back to life after a hard stretch...some of the best skating i've ever done, i did in and because of that city...i am the truest believer.
although Detroit will always be my home and the truest skate city to me on a personal level, Chicago in my eyes is the skateboardingest city in this country...and i say that after having lived in SF a couple of times.
also, although i know he doesn't care too much about this kind of thing, Junior "JuneBug" Gonzalez is the truth--does SO much for Chicago skateboarding and for all of the "shorties" from the city...