I'm planning on it for my next WDW flight. DD and I both have food intolerances, and while I can make do fairly well - she can't. So I'll be packing homemade gluten free mac and cheese, frozen pancakes and a few other staples in a 5 hour insulated bag with plenty of ice packs. Since it is soft sided and zipable I'll just put it inside a suitcase and it can be inspected by the TSA or whomever.
I don't know how you'd seal a regular cooler such that it could be TSA or airline inspected/resealed and not open with normal handling. Also, I'll be traving in December on a direct flight that's about an hour and a half gate to gate, and won't be using ME and will have a fridge/freezer to move the food to when I arrive. I wouldn't try this in the summer, with connections or with a significantly longer flight, although people have been successful with longer flights.
Another (more expensive, but more reliable) option might be to send it fedex overnight to your resort with plenty of ice packs and plenty of packing peanuts for insulation. Several of the online allergen grocers use that method to send frozen foods with good success.