Airtrain/Subway or Cab from JFK?
 

We arrive on a Tuesday at 4:40 PM (Yes, timing sucks) but that's the way it is. SO, which would you suggest - cab or Airtrain? I know the cab will be much more, but if it's a lot more convenient, then we can pay

There will be 4 of us - 2 women, 2 teens (17 year old girls). I think much of this answer also depends on how much luggage they have. I"m a light packer but not sure of the others....

Forgot to add, going to Midtown East.

If there is a lot of luggage involved I wouldn't use Airtrain. The cab will be a flat $45 + tolls + tip. For planning purposes figure $60, and you'll have the convenience of being dropped off at the door of your hotel. When you land collect your luggage and just follow the signs for "Ground Transportation" and queue up in the official taxi line outside. We have often put 4 in the cab plus luggage in the trunk with no problem.

With 4 people, the cost is actually a wash. You'd likely pay about the same.

Even still, I'd suggest the Airtrain. At that time of the afternoon the traffic into Midtown can be atrocious, and the trip might take well over an hour. You may or may not save money with Airtrain, but it will be at least half the time into Manhattan. This way you just have to pay for a cab from Penn Station to your hotel and (hopefully) be able to do the trip in 15 minutes or less if you get lucky with traffic.

I do want to be clear that you cannot easily take the subway or bus to your hotel in East Midtown, and it would save you pennies. But it's very crowded at that time of day.

If your traveling companions have a lot of luggage, though, a cab is the only realistic alternative (i.e., anything over a 22" suitcase). Good luck.

Airtrain to LIRR will save you some time over Airtrain/subway, and the transfer distance at Jamaica will be shorter than going to the subway.

I'd take a taxi. It makes no sense to me to go to Penn station and then have to back track to the east side. The fixed rate on the taxi means it doesn't matter how bad the traffic is. Just relax and enjoy the ride. With 4 of you, absolutely no reason to be schlepping bags in the train.