I would suggest by passing Chicago by traveling to Manitowoc WI to take the Ferry across Lake Michigan to Ludington Michigan. In Manitowoc, there is a Maritime Museum of Great Lakes, includes how submarines for WWII were built there. Once in Ludington, swing north to Traverse City explore wineries. Head across Mackinac bridge and drive to Whitefish Point to visit the Great Lakes Maritime museum. Great stuff on the Fitzgerald. Heading west, stop at Picture Rocks area, beautiful stop plus opportunity to go out on glass bottom boats for wreck tour.
Gaylord Michigan visit Jays Spts. Really nice place.
Just a thought! Enjoy your trip!