Due to the unusually warm weather here in the Midwest, I was able to do a short tour in Illinois with my son just a couple of weeks ago during his spring break. Essentially we took Amtrak from Chicago to Carlinville, IL, then rode north (with the help of a tailwind) until we hit Princeton, IL, and we took the train back to Chicago from there.
5 days of travel, 4 full days of biking, around 250 miles (most of which was on low traffic township and county roads), all in all a great time.
I have wanted to do a long tailwind ride with the help of Amtrak for some time now, and it worked out really well.
Here's a fuller journal of the trip for anyone interested:
http://www.crazyguyonabike.com/doc/?..._id=10337&v=6P