Hello everyone! I live in central Montana and am in the process of buying a car from a private party in Chicago, and could really use some help planning the drive home. The plan is to pick it up on Friday May 25th and drive it home (solo) over Memorial weekend. If all goes well I will be leaving Chicago mid-afternoon Friday and would like to arrive in Billings by early evening on Sunday where I'll stay the night with family before driving the last few hours home on Monday. This seems fairly doable with one problem - I'd very much like to drive the Beartooth Highway (weather permitting) which forces me to maximize driving time on the previous day, which I'm not sure is wise.
So, without further ado, here is my tentative route...
Day 1: Friday 3pm - 8pm
Chicago, IL to La Crosse, WI (283 miles)
Day 2: Saturday 7am - 7pm
La Crosse, WI to Spearfish, SD (683 miles)
Day 3: Sunday 7am to ?
Spearfish, SD to Billings, MT via Hwy 212 (~500 miles)
Obviously the stretch across South Dakota is pretty long. My plan is to break the day up into multiple chunks, stopping frequently to stretch my legs, and not pushing myself too hard. If I start to feel fatigued I intend to stop for the night (Kadoka, SD or thereabouts) rather than push through. In all likelihood this would mean skipping the Beartooth section on Sunday and going straight to Billings.
So what do the experts think? Am I crazy to even attempt this? I consider myself to be in pretty good shape, and am definitely a road trip enthusiast, but it's been a good many years since I attempted anything quite this long. I did recently drive a moving truck from San Francisco to Montana with my wife and our three year old, which was an awesome trip, but we only drove about 6 hours per day. I'm afraid I might be overreaching based on how well that trip went.