We learned early on to allow our DD to book her own flights to and from the Academy.
Your soon-to-be-cadet will know their schedule best as well as what transportation is available to get them to/from the airport, sometimes it is "Cadet Taxi".
Our DD has a credit card in her name that is actually my account for this purpose as well as emergencies. Some parents may not trust their DS/DD to be that financially responsible, but we have done this with both daughters (while the oldest was is college several years ago) and have never had a problem of misuse.