Here's a great ride - start out from the East around Hillisde, IL (further East if you're brave) on the Illinois Prairie Path, ride out to Villa Ave. in Villa Park, turn right, go 2 blocks and hit the trailhead for the Great Western Trail, right in front of the old Ovaltine plant.
This great trail leads you down a straight shot west to West Chicago, where it reconnects with the Elgin branch of the IPP. Along the way are great city parks, some really cool residential areas, working water fountains, and, best of all, the Churchill Woods!
Churchill has a very diverse layout, with a plant and tree nursery on the north end along the Great Western Trail, then tall grass prairie, thick forests and finally marshy wetlands as you ride South. There are picnic shelters, a Forest Preserve District maintenance facility and even an island in the middle of the DuPage River.
There are established doubletrack trails which you can connect to at Swift Road and the GW Trail. There is remarkably NO singletrack in this preserve whatsoever, but the main trails take you wherever you want to go in this great preserve.
This is a great destination if you are looking to get in 25-30 miles in an afternoon. You can connect with the IPP from the CTA Blue Line and ride it all the way West from First Avenue in Maywood, IL., but the residents of Maywood and Bellwood are more interested in breaking bottles on the trail than riding on it, so I recommend starting a little farther West.