Here are some local groups we support that also have good sites for rides, events, etc:
CAMBR.ORG (Northern Illinois affiliate of IMBA) Great source for local trails, and how to help CAMBR build more trails in our area.
www.BikeLIB.org (League of Illinois Bicyclists) - Illinois charity rides and bicycle safety advocate
*Also check out their bike safety quiz - www.bikesafetyquiz.com
activetrans.org (Active Transportation Alliance) another great local bike advocacy group that produces the best bike/street map of Chicagoland.
Facebook: Sasquatch Squadron - Main Street Bicycles racing team - focused on Cyclocross
chicrosscup.com - Chicago Cyclocross Cup series site
foxrivertrailconnections.org CMAP Bikeway Feasibility Study