I don't know how it works for pilots, but a lot of musicians I know stay at the Days Inn on Soldiers' Field road. Not really close to the airport (6 milesish), but most likely affordable if poor music folks stay there.
Thanks for all the tips. Our trip went well...the Fairfield Inn in Tewksbury offered us the Gov/Mil rate of $69 with the Airline ID...I thought that was pretty nice of them. Clean, comfortable and free breakfast.
I've had good luck with Budget rent-a-car for the 4th time in a row now using our airline discount code in various parts of the country. DRO, BOS, HNL, and CHS.
Getting to and from BOS via car was a lot easier with the tunnels...I grew up on the central artery which sucked bigtime!