South Florida To Seattle Washington

[Midwest Michael]

I'm really confused, when you initially posted you talked about driving just 5-6 hours a day, now you're saying your in Kentucky and planning to get to Omaha next - which is 10-11 hours away and the upper limit of how far you should travel in a day - and that's assuming you're at the Kentucky/Illinois border.
Then you're talking about going from Omaha to Billings, which is about 850 miles and about 15 hours on the road, and nearly 50% more than you can safely travel in a day.

So beyond the obvious that you need to stop well before you get to Billings, you also need to rethink your definition of mountains. It really isn't a case that you go up a big hill and then come down and you're done - you'll be going over a few mountain passes, but also several more smaller hills, starting when you go through the Black Hills (which are actually mountains) in South Dakota.

Billings is a perfectly good place to start before you head into the most significant mountains of Montana, but you'll need to stop someplace before that - perhaps Rapid City or Wall SD.

Similarly, if you stop in Billings, you'll need to stop again somewhere again before Seattle - Coeur d'Alene, ID could be an option.

[ToInfinityAndBeyond]

Sorry, I posted my reply in a rush. We’re heading to a bit outside of Omaha and it’s near 8 hours but after that, we are taking 2+ days to Billings. Would it be advisable to stop in Billings or Bozeman? And yes, we were planning to stop in Spokane or Coeur.

[jm98]

How is trip going? Have you made it to upper midwest yet? What's weather like and driving conditions?

[noFanofCB]

I don't see much difference between Billings and Bozeman other than the distance between them. It's pretty much river bottom highway between the two except that there can be ferocious winds at Livingston (2nd windiest place in the US I think). There is a bit of a pass west of Livingston but it's just one of many on I-90.

One thing I know from personal experience is that you might rather not overnight in Butte because it seems to be 10F colder overnight than either Missoula or Bozeman. That can make a big difference when temps are going below zero. (I had a -30F start one morning one December.)

[Midwest Michael]

Any of the cities you've mentioned would work for overnight stops, but considering your statements and where you are now/are planning to be, I think Billings/CdA make a lot more sense.