Way back when I was riding a lot, there was a route from Lyon Oaks Park in Wixom to Kensington Park and back. That usually included a few of the trails in Kensington as well. Not a great distance, maybe about 10 miles or so. Then work got in the way again.
One of my favorite rides in the Chicago area was along the Illinois and Michigan Trail. This was back when they had just started building it. I attempted 50 miles on my 50th birthday, probably finished 30 out and back. A very humid July day.
I did spend a bit of time on the Prairie Path out of Lombard and Aurora/Naperville. Our apartment in Lombard was right off the path, as was the house in Aurora.
I really do need to get the bike out again. There are a few nice rides around here.