I've gone both ways. I will never go via Chicago again if I can possibly avoid it. The congestion & tolls are ridiculous. I-75 thru Michigan is easy, & the Macinac Bridge is an experience in itself. I think 28W & 2W are the routes across the UP & Wisconsin. Nice rural driving as long as you don't get stuck behind a logging truck. Some nice small towns, & some nice scenery along Superior. Mapquest.com is pretty accurate for estimating mileage & time. Any trip heading north to Q is a good one. :)
WiF