I stayed at the Crown Plaza Hotel in Madison, Wisconsin. Beautiful hotel. If you call Hotwire.com along the trip, they can easily get you a room that night, close to where you feel like stopping. I would book a room at Hampton Hotel in Pittsburgh, Pennsylvania the 1st night. The 2nd night I would book a room at the Hampton Hotel in South Bend, Indiana. The 3rd day will be 4-6 hours. Traffic can be slow around Chicago. I hope this helps. Safe travels.