Would be happy to see you while you're in Chicago, if there's time!
Personally, I prefer Wisconsin to Michigan, but either way, stick close to the lake. If you go up through WI you could stop in Door County, which is a picturesque peninsula that sticks out into the lake, then drive through the UP and head into Canada near Sault Ste. Marie. On the Michigan front, you have a choice between driving up the west coast to Sault Ste. Marie, or hitting Canada at Windsor, near Detroit. The latter would be quicker but much less interesting--Chicago to Detroit is a really boring drive, but it's only about 5 hours, whereas you could take 2-3 days going the long way around.
Going through Sault Ste. Marie would give you a chance to stop at Mackinac Island. There aren't any cars allowed on it--you'd have to take a ferry--but its Grand Hotel is very famous.
If you're driving near the coast of any of the Great Lakes, you shouldn't have trouble finding little towns to stay in. You might want to track down some lighthouses.
And once you're east of Michigan, I'm no help. [g]
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Personally, I prefer Wisconsin to Michigan, but either way, stick close to the lake. If you go up through WI you could stop in Door County, which is a picturesque peninsula that sticks out into the lake, then drive through the UP and head into Canada near Sault Ste. Marie. On the Michigan front, you have a choice between driving up the west coast to Sault Ste. Marie, or hitting Canada at Windsor, near Detroit. The latter would be quicker but much less interesting--Chicago to Detroit is a really boring drive, but it's only about 5 hours, whereas you could take 2-3 days going the long way around.
Going through Sault Ste. Marie would give you a chance to stop at Mackinac Island. There aren't any cars allowed on it--you'd have to take a ferry--but its Grand Hotel is very famous.
If you're driving near the coast of any of the Great Lakes, you shouldn't have trouble finding little towns to stay in. You might want to track down some lighthouses.
And once you're east of Michigan, I'm no help. [g]