Flying out of Stamford is a bit of a hassle. :) I try to reduce the hassle as much as possible. For those new to the city, let me review for you the choices you may have when leaving this fine city for JFK or LGA. (I disregard White Plains, even if it is more convenient. You simply cannot trust it to always be able to fly you where you want to go.)
In any event that you leave for JFK or LGA, plan to leave at least 3 hours before departure. The reasons will be most evident in a moment:
1) You can use the public transportation route to get to JFK/LGA. This is the cheapest route but the most time consuming. Both routes involve taking the Metro North to Grand Central. From there you can take a direct bus to either airport or use the public bus system to LGA or the subway to Penn Station/AirTran to JFK if you're really a cheapskate. Either route will take 2 hours if you get the express, 2.5 if you get the local. If you have a morning flight (<9 am) forget it; you won't make it in time.
2) Driving there yourself. This is a bit more expensive, and due to more exhorbitant fees for parking and the higher cost of gas, may not be the most economical for a long trip. Google lies and says that the trip takes 41 minutes for LGA and 50 minutes for JFK; however, traffic will double the length of time, although in the morning this is easily the fastest method.
3) Getting someone else to drive you. This is by far my preferred method. :) If you are without friends who will help you out (take the googled number in 2 and multiply by 4 and think again about asking a friend to drive that) then there are services that will drive you there and pick you up. I used to use CTLimo but now I use Red Dot because it's more convenient. Yeah it costs 60$ one way, but if you company compensates you this is a no-brainer, and it may be cheaper if your trip is longer than 2 days.
There you have it. The only ways to get to the major nearby airports guarantee that you will be travelling for at least 2 hours before you start travelling, or end up paying for the priviledge. Except for one amazing exception, I've never had problems with my flights. Feel free to send me whatever horror stories you have about your airport experience (especially if it was local so we can learn about it here :D) If I get enough responses, I may regroup them and publish for everyone to see, and in the process include my sole exception.
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