I dont know what part of Indy you are from, but with customs and immigration delays, luggage, traffic, gas costs, travel time, construction on EVERY highway between IN and IL, possible delays on a west bound (into the wind) itin, quality of life being stuck in a car, etc...I would just let him stick with the flight to indy. You will be less tired and most likely (and I say this from experience driving that route) you will be home earlier.