We also just came back and just flew for the first time with our 2.5 year old. She did great on the plane. Prior to our trip, I kept explaining to her about the flight and made it sound really exciting. I brought some little toys that were "new" to her which kept her entertained. We also brought a portable DVD player which was definitely a life saver. I'm not sure if her ears even bothered her, but we put in these things called EarPlanes for her which I bought from the One Step Ahead website. Not sure if they worked or not, but they did seem to make her happy. The one thing that I wish I spent more time preparing her for was the check-in/security process. She was fine when we were leaving out of Boston to go down, but on the way back had small meltdowns when she had to take her sandals off to go through security. Since you go through security twice in Aruba, that made for 2 meltdowns. Oh, and we did not have a car seat for her and she was just fine. So, the things for us for the flights were new toys, dvd player, and snacks. Good luck!