Sorta...about 30 miles SSE of CXR but I've crossed that lake enough in singles to know where those islands are.
I'd still recommend the long way, but if you're committed to doing this in the shortest distance possible, go as high as you can (take O2 if you can and go higher) and cross the lake at the narrowest part...over the islands will work if you're high enough. If you can get in the 12-14k range, you should be okay. Keep in mind that icing will be a factor this time of year.
I used to cross at 12k going up to DTW out of BKL in the caravan and I'd go over the islands going into BKL from DPA descending through about 15k at that point, IIRC...some nights I'd stay low but never lower than 8-10 depending if I got sent over CGT or LEWKE on the way out of Chicago. As much as I could tell with my math, I could either make the "mainland", the islands or Canada (BKL-DTW) at any given time. ATC was always very helpful and understood the whole single engine/cold water/hypothermia thing.
Go IFR and you shouldn't have much of a problem. I've got an FCC license, but I'm not sure if that's required or not. You'll probably talk to Cleveland Center the whole time, so I don't think Canadian ATC will come into play. If it does, just be ready for the "lingo", like "Radar Identified" vs "Radar Contact"...things like that.
Still, going over TOL and heading East from there would be my recommendation. Make just very slight cuts off of the corner of the lake. No more than you can glide to shore from.