re: Madison or Milwaukee

Madison is a nice city. The campus is actually integrated into a very vibrant downtown in terms of activities, restaurants and nightlife. It's pretty akin to Baton Rouge in terms of being a capital city with the state's flagship university.

Milwaukee is more of a big city feel than Madison and is about 30m closer to Green Bay. Flights are going to be much cheaper into Milwaukee as well as Madison is notoriously expensive to fly into.

While Chicago might say it's a 3h 30m drive to Green Bay, that is extremely dependent on time of day as traffic can be a bitch around Chicago. That's the only thing I would be hesitant about in terms of staying in Chicago. Flights into O'Hare are also going to be much cheaper than Madison and probably cheaper than Milwaukee.