After some research, here is the preliminary calendar for most CX events of interest, plus some road trips, in the general proximity of Illinois.

09/20/09 Sun CX Jackson Park Chicrosscup
09/26/09 Sat CX Madison, WI Planet Bike Cup
09/27/09 Sun CX Madison, WI Planet Bike Cup
10/04/09 Sun CX Dekalb Chicrosscup
10/11/09 Sun CX Hawthorne Woods Chicrosscup
10/18/09 Sun CX Carpentersville Chicrosscup
10/25/09 Sun CX Bartlett Chicrosscup
11/01/09 Sun CX St Charles Chicrosscup
11/08/09 Sun CX Northbrook Chicrosscup
11/14/09 Sat CX Indian Lakes Chicrosscup
11/22/09 Sun CX Woodstock Chicrosscup
12/06/09 Sun CX Montrose Chicrosscup

11/29/09 Sat CX Jingle Cross IA
11/29/09 Sun CX Jingle Cross IA
10/03/09 Sat CX ?? WI Cross
10/04/09 Sun CX Lapham Park WI Cross
10/10/09 Sat CX Grafton WI Cross
10/17/09 Sat CX Badger Prairie WI Cross
10/18/09 Sun CX Cam Rock WI Cross
10/24/09 Sat CX Janesville WI Cross
10/31/09 Sat CX Halloween CX. Milwaukee WI Cross
11/08/09 Sun CX Estabrook Park WI Cross
11/14/09 Sat CX Kletsch park, Milwaukee WI Cross
11/22/09 Sun CX Hales Corners, State Champs WI Cross

10/04/09 Sun CX Devils Cross Quad Cities, IA
10/11/09 Sun CX Vande Cross Quad Cities, IA
10/25/09 Sun CX Psyclofest Quad Cities, IA
11/22/09 Sun CX Middle park Madness Quad Cities, IA

10/24/09 Sat CX Derby City Cup, USGP Louisville, KY
10/25/09 Sun CX Derby City Cup, USGP Louisville, KY

10/09/09 Fri CX Cincinnati CX Festival Covington, KY
10/10/09 Sat CX Cincinnati CX Festival Middletown, OH
10/11/09 Sun CX Cincinnati CX Festival Fairfield, OH

(Edited with new Indian Lakes Saturday Date)