Thank you for all your tips. I'm forwarding this thread to him. I most agree with the options that have him going EWR-ORD with a stop, maybe these few weeks that are already scheduled LGA-MDW will convince him that it is occasionally worth taking a flight with a stop.

As for the Continental suggestion, I knew about that, but his corporate travel computer (based on company policy) seems to have effectively banned CO unless it is the only airline that goes where you need to go. Even to the point where a continental flight was $9 less than an AA flight, and yet was still out of policy. Crazy!