Chicago by Bike
For a 40 mile radius around Chicago there are great places to go ride. These are a collection of roads and trails I think are worthwhile doing for everybody in Chicagoland that likes riding their bike.
Explore the Collection on Ride with GPS
The Lake Michigan Ferry Tour
A self supported 5 day bike tour around the lower half of Lake Michigan.

Illinois Prairie Path / Fox River Trail
Endless miles of mixed surface trails through the western suburbs.

Sheridan Road
Ten miles on one of the best cycling roads through the North Shore.