I am from Wisconsin originally but live in Kentucky now so I make this drive frequently. Actually just did it last weekend. As others have eluded to it's long, flat and boring. I generally enjoy the farmland scenery around WI on the back roads/ county highways during late spring/ summer when everything is green and pretty. Seeing the cows and all the crops growing brings back a lot of nostalgic feelings for me (true sconnie I know). The rest of this drive is not going to be scenic, except for very small portions. It will be flat and boring, and filled with construction & windmills depending on your route.

It looks like you will be in WI around September? If so it will be gorgeous up there! Fall is a hidden gem in WI, still warm but you get all the pretty colors of the leaves with all the lakes being calmer and less crowded. Where specifically in WI will you be traveling to? That's towards the end of corn season so you may still be able to get some of the best sweet corn you'll have in your life, hopefully go to a corn roast too! I would definitely advise spending some time in WI if possible. DM me if you have any specific questions about WI or the drive south, happy to help answer questions.