I'm well aware of the travel time and challenges between IND and ORD, having traveled it quite frequently myself. There's no chance of the luggage staying on the flight, since ORD is his first touchdown in the US, therefore necessitating him taking his checked bags through customs and then re-checking them for the flight to IND.

We'll decide based on the weather when the day arrives and will check with AA before making a final decision.

Thanks again,

GG