
Originally Posted by
Midwest Michael
I'm confused about how much time you actually have available. In your original post, you mentioned 14 days, but the 22nd to the 1st would only be 10 days. (With just 10 days, then Chicago really isn't something I would consider)
As others have mentioned, I would be careful not to overextend yourself, especially this time of year when there are limited hours of daylight available. Traveling 500 miles in one day is not a big deal at all, but if you're planning to travel 400-500 miles a day every day, you look like you're quite close to running into a situation where all you are doing is driving nearly from sun up to sun down every day, without leaving much time at all to see or do anything at the places you are looking to visit.