You can technically do this:https://www.trippy.com/drive/Chicago-to-Chapel-Hill-in-3-days
But it's basically giving you the same stops, just breaking up the trip into 3 days with 2 overnights.
Now if you want to explore more stops, you can search each day on its own:https://www.trippy.com/drive/Chicago-to-Richmond-IN-in-1-dayhttps://www.trippy.com/drive/Richmond-IN-to-Charleston-WV-in-1-dayhttps://www.trippy.com/drive/Charleston-WV-to-Chapel-Hill-in-1-day
That gives you a lot more possibilities along the way. Hope that helps!