$270 - Round Trip Flights to Boston on Virgin America

Flight Details: Virgin America recently announced round trip flights to Boston from San Francisco. United and American Airlines also offer flights for under $300, but the flight experience is much worse, and they have layovers in cities that are often out of the way. Details

Timing: This particular flight is in early May, but you can find these deals on most days any time in the next three months.

What to Do in Boston: The best bars in Boston tend to be for sports fans, though for big night you can also go to Fanueil Hall or Newbury Street. For live shows and dive bars, head across the Charles River into Cambridge. Kendall Square and Central Square are two of the most vibrant neighborhoods in Cabridge. According to many long time Bostonians, Harvard Square is losing its character.

For more information about what’s going on in Boston, check out any of these sites:

Boston Phoenix
Boston.com
Bostonist
Boston.Going.com

Especially starting in May, many of the surrounding areas in Boston start filling up with party-ers plus anyone looking for a relaxing time. Newport, Rhode Island and Portland, Maine are both only a two hours drive from Boston.