If you have the legs to make it across Canada, a really nice stop is Clare Mi. 48D. Great gas prices, crew car, ice cream in the fridge, a nice place to stop. If you don't land, Canada overflight only requires you are on flight following,
I typically cross the lake at Ludington, Mi.. It is the narrowest part. I cross at 10,000 and on a good day am only out of sight of land for a few minutes. Hazy days can be 20-30 min with no land, and sometimes even no horizon. So be ready for VFR/IFR flight if necessary. I typically start a long decent about 1/2 to 1/3 of the way over to add speed. You need to be down to 1800 or 2300 feet by Ripon anyway.
If you don't have the legs to overfly Canada, it is best to stay south of the lakes and come up the Chicago waterfront. A beautiful flight. I have had problems with weather coming off the lake. Clouds seem to pile up along the waterfront sometimes.
Good luck!