For those with appointments who will be flying, recommend you get used to Southwest Airlines, and think of how your cadet will navigate the Uber, train, airport options when they attend without you along for guidance. For example, during the school year, cadets are released until after their LMO (Last Military Obligation) and during finals the release dates vary based on your final schedule so you will either buy a ticket very late at high cost when the final schedule rolls out, or buy one early on the cheap and change it. With Southwest, there are no change fees, so you can adjust based on your cadets final schedule. Providence is a $60 Uber and cadets carpool often reducing cost. Hartford is an option, but further away. Boston via Amtrak is possible, but again can be logistically challenging and while a schedule may look good on paper, with Amtrak delays, weather, etc. can be tough. Owning a car is only an option for seniors (1/c) cadets, so public transportation is the thing.
We have tried all three airports several times, and by far the easiest logistically is Providence airport, but you will probably get a connecting flight home, not nonstop. Don't forget to factor in Northeast weather especially for winter break.
Tip - let your appointee set up the travel and navigate the airports, it will be good practice for the school year and they will be more familiar with whatever option you choose when they travel home alone during the school year.