Chicago to Billings in 2.5 Days via Beartooth Hwy: Pushing too hard?

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.

Welcome to the RTA Forum!

I don't think you are crazy, but I don't really understand your logic either. The Beartooth is on the wrong side of Billings and adds 200 miles to your trip. I'm not even sure your plan to get there. The fastest way from South Dakota to the Beartooth would actually be to go through Billings, although I'm guessing you'd maybe go to Cody first and then loop back? You might be able to do it, but trying to do those 500 miles on your last day, on mountainous 2 lane roads really won't give you time to savor these great drives.

And you are right that LaCrosse to Spearfish is a very long day on the road. I would either try to push a little farther, to say Rochester MN on night one, or stop shorter at Rapid City on day 2. Having said that, trying to get out of Chicago on Friday of a Holiday Weekend will likely mean heavy traffic and longer than usual delays, so keep that in mind too.

Since you live in Montana, Wouldn't it make more sense just to save the Beartooth for a weekend trip later this summer, maybe take an extra couple days and spend some time in Yellowstone while you're there?

Perhaps a better option would be to use your time to explore some of the Badlands and Black Hills? It seems like you've basically got a half day extra to work with, and I think exploring what's right on your way would be a better use of your time.

BTW - we may run into each other on the road! I'll be driving from Madison to LaCrosse on the same evening you're planning your drive.

Thanks Michael, your points are well taken. Perhaps I can explain my logic by admitting that there is none! It probably doesn't make sense to swing wide through Cody, but I was hoping to do just that because the Chief Joseph highway from Cody to the Beartooth Highway junction is another beautiful section of road. It's likely the case that I'm just trying to shoehorn in too much driving because opportunities like this don't come along as often as they once did.

Thanks for the heads up re: Chicago to La Crosse as well. I'm still undecided as to that route, weighing options for scenic off-interstate routes against holiday traffic delays. I had been advised to try Beloit to Prarie du Chien and up to La Crosse for the scenery but I'm just not sure. Could these more circuitous routes actually be preferable, given the holiday traffic through Madison?

Beloit to PdC would take quite a bit longer than going via I-90, at least an extra hour really. Southwest Wisconsin is very hilly, so there's not a lot of good route choices that aren't going to be quite slow. In fact, if you are thinking of something like that, I'd take US-20 from Rockford to Dubuque and then head north (or continue on US-20 across Iowa, which is 4 lanes for much of the drive).

Madison's traffic isn't too bad, especially if you are on the interstate. It will really be just getting out of Chicago that's the problem, especially since you'll have a ton of people heading north for a vacation. Once you are out of Chicagoland, you'll likely see heavy traffic and slowdowns, but you shouldn't be dealing with any stop and go traffic unless there is an accident.

If you do want a scenic detour, you could take US-14 from Madison to LaCrosse. I go this way when I'm not in a hurry and want a change of pace - its nice and scenic and only takes about an extra 30 minutes vs. I-90. The only warning is that if you hit Madison between 4-6pm, I would not go that way because you'd have to take US-12/18 (aka the Beltline) to get to the west side of Madison, and that can be gridlock during Rush Hour.