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Bradley is smaller, less congested and easier - but many of the flights to and from are a little more expensive (though Southwest has many great deals at BDL).
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Do you mean BDL is smaller than Westchester? Westchester (HPN) is about 6x smaller than BDL. Not only does BDL offer more flights to more destinations and more airlines, BDL handled over 6,000,000 passengers to HPN's just under 2,000,000 in 2008.
HPN has service to about 15 cities while BDL has service to around 40.
Anyways, IMO BDL is about the best choice for anyone in Connecticut except far southwestern Connecticut, and that is debatable.
You can make the connection from Metro North to either Newark, LaGuardia, or JFK but it takes anywhere from 1-3 hours depending on where you are coming from.
I sometimes fly into JFK because I prefer jetBlue. I fly into JFK and take the AirTrain to Jamaica Station. From there you take the Long Island Railroad into Penn Station. From Penn you would then take the subway (you could take a cab for about $10) to Grand Central. From Grand Central you would then take Metro North into Connecticut.
Another option is to take the Subway from Jamaica station directly into Penn or Grand Central but this adds a good amount of time.
Yet another option is to take Amtrak from Penn Station. While this is the fastest option, it is also the most expensive. You can take Amtrak directly to Newark airport without any connections besides the airtrain @ the airport station. You can also take New Jersey transit from Penn Station to the EWR station as well.
Stick with BDL unless you want to fly jetBlue. If Westchester fits where you are flying to fly from there if needed. Westchester does have a decent amount of Florida flights which is what really got the airport off the ground 10 or so years ago.