If the Falls and Volk MOAs are cold in central Wi, something like JOT DLL EAU would probably work well. If the MOAs are hot and you can't get through, well, that's a hassle.
Volk approach may vector you through the MOA even if it's hot, or at least around the restricted areas that are up there.
If that's not the case, you'll wind up going west (JOT ODI EAU or something) or east (OSH STE) around the MOAs.
You can try direct, who knows, you might get it. It is helpful to include a point within each center's airspace to keep the computers happy. Just remember that the points that define your route become mandatory reporting points if you hear the magic "Radar contact lost" words.
Radar coverage is pretty good up there so that shouldn't be an issue.
I usually file to an initial approach fix or start of a transition if it looks like I'll have to fly an approach on arrival.
As for getting through Chicago, well, might as well plan to go around and be happily surprised if you get more or less straight through.