Flying to Boston is super convenient. I do it a few times a year. We have a couple airlines with direct flights. Not only is that faster, but also cuts down on the potential for things to get messed up with missed connections and lost luggage and whatnot.

As for where to stay in Boston… really anywhere that’s close to a subway line will be good. The Blue and Silver Lines take you to the airport. The Green and Orange Lines connect to the Blue Line, and the Red Line connects to the Silver Line. Blue Line is faster and easier but if it meant saving $50 I’d take the Red/Silver without giving it a second thought.