Help me plan my next cross country route

[BrooklynMW]

It's time to update my sig. I want to add a 3rd squiggly line across the map. (Think maybe I'll go with green this time.)
But in order to do that properly, I need to make another run across country. I ship out first week of Feb. Was thinking of going north this time (if the snow stays away). Never been to Chicago, wanna visit a friend in Rapid City, see Mt. Rushmore, Devil's Tower. Then head to PNW and down to coast on PCH to San Diego.
A little ambitious, I know. But I'm open for suggestions. Looking for interesting stops, great towns, great food. Also a couple of mid-trip checkups.

Thanks!

[Eric]

that's sketch in the winter to take the northern route. Do you have proper snow tires (not all seasons). Are you Navy, or Merchant Mariner?

[Ninz30]

I have buddies in the northern states who say it snows in April!

[BrooklynMW]

Yeah I know. I'm gonna be checking weather conditions before I go. I can always take the southern route again. No snow tires. Actually I been thinking about some Yokohama S.Drives, which I know are not fit for cold weather, but once I get to Cali, I won't need to worry about that. Could use the tires I have on my car, but I want a nice smooth ride.

No, I'm not in any kind of service, ha. Just used the term "I ship out" quite loosely I suppose.