
Originally Posted by
glc
Welcome!
Chicago to Jackson via fastest route (mostly Interstates except in Wyoming, I-80 to US-191) is 1400 miles and is a 2.5 day drive. Going via Rushmore (I-90 to Rapid City) makes it a full 3 day drive with very little time to actually spend there. However, the Rushmore area would make sense for an overnight stop - with Sioux Falls being the other overnight. You can make it from Rushmore to Jackson via a few different routes in 1 day, but it will be a quite long day.
If you want to sightsee on this trip, I'd advise you to add a day at either or both ends.