More Balanced than Many I've Seen
Bienvenue sur forum de RoadTrip Amérique.
Your itinerary is quite ambitious, and may turn out to be a bit much depending on how well you and your family tolerate long hours in the car. In particular the Chicago to Sioux Falls segment is about 575 miles (920 kilometers) and many of your other legs are 350-400 mi (550-650 km). I'm just afraid that too many such days will begin to take their toll on your wife and daughter. But if you are all used to such travel and you plan to take several short breaks on your driving days, you do seem to have enough places along the way where you stop for a few days to catch your breath, and this should be a great adventure.
AZBuck