How about Barrington to Madison?
First, take the Metra (the only way to fly) NW line from Chicago to Barrington.
http://metrarail.com/Sched/cnw_nw/cnw_nw.shtml
Then, take this route from Barrington to Lake Geneva,
http://www.chicagotriclub.com/info/directions.asp
Then, use these maps to get from Lake Geneva to Madison, they are very accurate in terms of biking conditions,
http://www.dot.state.wi.us/travel/bi...countymaps.htm
You will go through Walworth, Rock and Dane counties, you may go through Jefferson county as an option insted of Rock county