Sam,
just so you know, the weather around Chicago and a northern route you're considering around Easter March 27th, can be fraught with really crummy weather. Snow would not be out of the question, but I can guarantee high winds, chilly temps and likely rains. You could consider the Grand Illinois Trail, 500+ mile loop that could bring you back to where you started. If you didn't want to go that far west, you can shorten the loop by heading north at the Hennepin feeder trail to Rock Falls, IL. Where ever you decide, have a great ride.
https://www.dnr.illinois.gov/recreat...usersguide.pdf