To the OP,
Everyone has pretty good pointers for going out of MSN>ORD in the winter. If I were you I would drive to MKE (more connecting flight options to other hubs UA and otherwise) or commute to ORD directly and leave plenty of connection time. For a SE asia destination I would fly west to maximize your connection opportunities, try to hit the west coast (less winter weather) or NRT as a next stop instead of IAH as your rebooking opportunities will be more numerous should the likely winter delay jam up your travel plans.
Another thought. When I was in college, I was quite successful using VDB's to gain elite status (gold at the time) on an us airline. At that time in my life I had the time to take later flights so readily volunteered for the next flights. The status was invaluable during IDB rebooking (since they have waitlist priority). I'm not sure UA does hotels for gold weather. I have had several domestic winter diversions that took 48 hours to get back on route and they only way I got back home on 3 occasions out of ORD because they IDB'd someone else (I was 1K on full fare at the time). Winter happens so you have to study the rules. Also, if you have UA *G you would get lounge access on your intl trips, priority phone access, and all the other stuff you can research.