Anything new is exciting and fun, so before you leave, go out and purchase a few NEW toys, books, etc. You can wrap them or not -- just keep them out of sight until you are actually in the air. Bring them out one at a time. When he gets bored with one thing you'll be ready with the next. These things need not be expensive -- the novelty of them is what works. The $1 bins at Target are a great source for stuff like this. When my son was about your child's age I brought along a book with tons of "lift the flap" things. It was great because it kept his attention for ever! You can see the one I got at Amazon http://www.amazon.com/Fisher-Trucks-Planes-Trains-Fisher-... Bring crayons and either coloring books or paper. You can use the snack tray and let him scribble away. I also usually bring a bunch of stickers (the foam ones are great too!). He can create a masterpiece with nothing more than a blank piece of paper. Also pack plenty of snacks -- things that are easy to eat with fingers and not to messy to clean up since he'll likely drop stuff. And although he is a little young for this, here is one more idea. Pack along some circular cereal (like Fruit Loops) and a shoelace. Let him string the cereal into an edible necklace. Between making it and eating it, you've bought yourself 30 minutes of quiet activity! Good luck and happy flying! :)