I ride from one suburb to the the next and it is pretty flat, just a couple hundred feet over 9.6 miles. There is a Forest Preserve with an asphalt path between home and work but I typically stick to the residential streets with one short jaunt on a 40 mph four lane divided road.
The ride home starts into the wind until the turn toward home will net me 12-15 miles for the trip. Every now and again, when time permits, I'll push the ride home to 20-25 miles.