I live on the northern tip of Manhattan (so far north, even Law and Order will call this area the Bronx). I generally use and love La Guardia Airport for its convenience. My advice to you is that before you consider ANY form of mass transit: bus or train, you take the luggage fully packed, find a building with four flights of stairs, and see if you can manage to get the luggage up those stairs not once, but several times. Then go to your mall, and walk up and down the mall for two hours with said luggage in and around all the crowds. While our system is being retro fitted with elevators and such, some stations have not been retrofitted, or if they have, they are not always in working order, or easily found. If you feel you can handle the luggage on a mass transit system, then my suggestion is to fly in and out of JFK. (Air-train to A train at Howard Beach transfer to the 6 at Broadway-Nassauâ€”the first stop on the A train in Manhattan). Then take the 6 train to Grand Central for the MetroNorth Train to Westport. The cost here is to and from Grand Central under $10.00 each way and probably 60 to 90 minutes in time. Trust me; this was not easy even when I was in my 30â€™s.
Therefore, I generally take a limo/car service to and from LGA at the cost of $40.00 each way for the car, and $5.50 for the TriBoro (aka RFK Bridge) plus tip. Taking a taxi from JFK will run $45.00 (plus tip) to any point on Manhattan with the same $5.50 toll unless you instructed the driver to take the Manhattan or Brooklyn bridge (which could definitely cost you more in the way of time.) Getting back to JFK from Manhattan is generally on the meter, but I would suspect would be around the same $45 plus tolls. If you fly through Newark, there is a shuttle bus to Port Authority at 42nd street and 8th Avenue that is probably running under $20.00 now-a-days. You would need to take a cab over to Grand Central at what I would think would be a cost of $10.00 or so.
As to the easiest, I do not fly in and out of Westchester airport, and I would take the advice of Ms Lipira who does, and go for LGA. I would rent a car, and then drive EAST on the GRAND CENTRAL (towards eastern Long Islandâ€”away from the city/the Grand Central is the expressway directly in front of LGA), I would take I-678 across the WHITESTONE BRIDGE then take the HUTCHINSON PARKWAY to the MERRIT PARKWAY (CT highway 15)â€”these two highways are really one and the same except the Hutchinson is in NY and the Merrit is in CT. If you miss the Whitestone, you have an alternative of taking the THROGS NECK BRIDGE to I-95/NEW ENGLAND THRUWAY. The difference of the two routes is that while the Merrit is a most ancient express way, commercial vehicles are banned from this route so you are not dodging the bulk of New England bound trucking. The tolls on the bridges are $5.50 each way. And I think there is a minor toll ($1.00 or so) on I-95/New England Thruway). If you rent, make sure you get a car with an E-Z pass, where the rental company will bill you for your tolls instead of having to pay them at the toll booth. The time savings are quite dramatic.
If expense is an issue as well, then you could fly in and out of Newark as rental cars and flights are generally cheaper at Newark. The reasons for this is that the cars rented in NYC generally come with some basic insurance coverage while it is an additional Per Diem charge in NJ. If you already have car insurance that will cover you when you rent a car then Newark is a better option. It is worth a call to your car insurance company. If that is your option, my best advice would be to take US Highway 1/9 WEST (again, away from the city) to the GARDEN STATE PARKWAY NORTH to I 287 EAST to I 95 NORTH to Westport, CT. This takes you around Manhattan, the George Washington Bridge, and most importantly, the Cross Bronx Highway. I think almost any New Yorker that drives in and around The City will tell you to avoid the Cross Bronx at all times. I know myself; I have been stuck on the Cross Bronx for two hours at 4 am. However, this route does take you across the Tappan-Z Bridge which sometimes can be a traffic nightmare. This option would cost probably 1 to 2 hours additional travel time over the LGA option.
Now with all of that said, the most important bit of advice I can give is do not under any circumstance plan an arrival or departure in rush hour. I would recommend flying in and out between 10am and 3 pm. And of course, I would be remiss if I did not encourage you to take a day for sight seeing here in The City here during the holiday period--especially after sunset. Everything is decorated and just spectacular.
I assume if you had an agent already you would not be asking this question. If you are considering moving here and need to travel frequently to Chicago for short hops, what I recommended above is the best in my experience.
From Laguardia, you have the option to rent a car or take transportation to Grand Central in the city for the train to Westport. Connecticut Limousine takes multiple people at a time and stops at different points along the route to Westport. Travel time by car is 1 hour with optimum traffic.
So where in the Chicago area do you live? What is your time frame for your journey back East?
If you are in need of further information, please feel free to contact me. I always look forward to meeting others from Chicago, my favorite city to visit.
PS Bradley is about 65 miles away and JFK and LaGuardia are about 28 miles away.
Enjoy your visit to Westport. It's a great town!
Fly into any of the big 3 NYC airports( JFK, LGA or Newark) or Hartford or Westchester....
Take a limo or rent a car based on your final destination...and what you intend to do during your stay...