Evansville is a tough trip. I was there numerous times years ago, and like you I tried to stay on DL. I drove from CVG, SDF, and IND. Once I went through STL on TWA (that tells you how long ago it was). If I were you, I would get a nonstop to the closest big city, and drive. I agree, there's nothing interesting on the trip, but you may get close to Santa Claus IN.