Two of Northern IL's best local cons are both coming up in November.
Rock-Con (Rockford) is 11/5-7 and Chicagoland Gamers CONclave is 11/26-28.
Rock-Con is pretty well known, while CGC is a bit of a 'secret'.
I've been to both before and probably will hit both again this year.
I'm tentatively looking at running a LARP and the long, long OOP TSR mini-game, They've Invaded Pleasantville at CGC.
CGC is in Bloomingdale (not Bloomington, which I used to always mix up when I was young), btw.
Also for Chicago-areaers - the Concentric folks have returned with two major local conventions, one coming up in early October.
http://rock-con.com/index.html
http://www.chicagogamecon.org/CGC_Home/Home.htm
http://www.concentricconventioncompany.com/product.html
The spring Concentric was excellent. It's too bad it was kind of sparsely attended - they had plenty of great events going.
Met Todd Breitenstein (Twilight Creations) who was running a Mega-Zombies game with $100+ in give-aways.
Won a copy of Tutankhamen (plenty of other games had prizes, too).
Favorite new discoveries were both from Mayfair.
Pompeii (not yet available in US) - move people in while it's considered a prime place to live, then help them flee when the lava starts to flow.
Entdecker - a tile/path + bidding game of sailing exploration.