During the winter we travel from Canada to the US and then onto Aruba. Generally, we go via Philadelphia but there are other options too. Which would you recommend as the best place to fly from in the winter: Philadelphia or Charlotte? I am asking about which location is least likely to be snowed in, etc. It is easier for us to go to Philadelphia but from where my kids go to school they have more options like getting to Charlotte direct (we have no direct flight to Charlotte). Other options are Dulles but there are limited Aruba flights. We can also go via Boston or Chicago but we haven't done that as a first choice as we know that they have more weather issues.
Charlotte is far less likely to be delayed than the other airports that you mentioned. The runways are laid out far enough apart that they can conduct simultaneous approaches or departures even in very poor visibility and the new runway should be open by now. That doesn't really come into play on most days, but would in the worst case scenario.
The biggest issue with Charlotte is probably going to be your connection coming home. The flight back from Aruba usually gets in later and may cause a tight connection to the last flight home. That does usually mean you get a little more island time on your last day and you don't have to rush to the airport first thing in the morning, so it does have its advantages as well.
The biggest thing to watch with Philly is your connection time. Always catch the first flight into Philly that you can and try to give yourself at least an hour to make a connection. Even if you are delayed a bit by the weather on your way in, you can till often make your connection if you give yourself enough time.
When I head to Aruba I often go through Philly, but I usually don't book my ticket until a couple days before the flight and have the benefit of knowing the weather forecast. If I had to book a couple months in advance, I would be heading through Charlotte every time. I like to eliminate as many potential problems as I can and Charlotte does that for me. Fortunately we have direct flights to both cities here and it doesn't involve any extra hassle on our part.
If there's anything I missed in my rambling or I created more questions, let me know.