My understanding is it open jaws count as one towards number of stopovers, but both points cannot have another stopover, but can transit again at either (as long as within 3 transfers).
If I understand your post you want to have xxx-ORD (stopover) -yyy-MKE/ORD-zzz I dont think you can do this, unless the flights between ORD and MKE are on a separate ticket.