The location is "close" to many places but is quite literally in the middle of nowhere by Italian standards. At the end of the day, you're not staying in any of the places you listed, so your ability to experience Italy will be very much curtailed. No cappuccino and croissant at the local bar in the morning, no late evening out carelessly strolling the piazzas until you're tired (without worrying when the next train leaves), etc.

O'Hare is close to downtown Chicago, the lakes in Wisconsin etc., but, to me, it's no place to stay on a vacation. YMMV, but if I were in you I'd consider splitting your night between a place like Stresa or Lugano and, after returning your car, Milano proper (take the train to Brescia from there).