Do you want to start now (Oct 19 at ~2:30 PM) or start the following morning? Tell me whether you want each driving day to be no more than 4 hours, or whether you want a single-day trip broken into 4-hour driving legs with short stops.
Tell me if you prefer the fastest route (I-80/I-90 / I-94), a more scenic route (through Michigan/Upper Midwest lakes), and whether you want hotel, budget, or boutique overnight options.