I know lots of airlines now have in-seat entertainment, so everyone has a wee TV in the headrest in front of them that offers tons of children's programming and films...it does depend on the airline though. i know Northwest, KLM, and British Airways (and American Airlines/Continental out of London) offer this, but if you fly from a smaller airport, like I fly from Glasgow, then the planes may not have that, but they always have a film which is usually family-friendly. Child meals can sometimes even be chosen in advance if you book online and select 'special meals'. I don't think he'll need a booster seat on the plane (come to think of it, I don't think I've ever seen anyone with one on a plane) but yeah, I'd google the lawss for the state you are visiting requiring the booster seat thing. The ipod nano is a great idea! I just got power-rangers action figures when I went on long plane rides years ago lol.