I've always flew out of LGA or JFK because I was only ten minutes from the airport (twenty to JFK). Now that I'm living out on Long Island, I absolutely will not, under any circumstances, fly out of The City ever again - even for a lower fare.
Now I live ten minutes from MacArthur and I will gladly pay the extra fifty bucks per head for the convenience of a leisurely five mile drive to a clean airport where I don't have to worry about anything - snarling traffic, long security lines, long check-in lines, etc.
You Know You will ALWAYS hit traffic on the way to JFK. I've flown into/out of JFK for fifteen years and Not Once Ever had we breezed through - And we lived in The Bronx which should only be a twenty minute drive.
IMO - You're getting ready to have a wonderful time on a vacation. Why mess it up getting all aggravated and you haven't even taken off from NY yet?
Yes, fares are more expensive, but you have to weigh your options. This is one area where spending a little more for convenience is better.
Take it from a seasoned Native New Yorker - Fly out of CT!