Eric,
Welcome to the forum ! I am in the Northwest suburbs, and there are some great guys here in the area I have met on this board :
bmussatti
djomlas
Chills
Sammy
super66
bmussatti, Sammy, and I just got back from the Tail of the Dragon 2 weeks ago :
http://www.986forum.com/forums/showthread.php?t=11047
http://www.986forum.com/forums/showthread.php?t=11087
http://www.986forum.com/forums/showthread.php?t=11169
djomlas, Sammy, and I are doing an autocross in Indiana this Sunday :
http://www.inr-scca.org/solo2/index.php
Haven't had a chance to meet Chills or super66 yet, but they seem like great guys.
Also, look into joining Chicago PCA :
http://www.pca-chicago.org/
Did a Rally with them this weekend. Older crowd ( I'm 36 ) but everyone was really nice...
Nick