I spent twenty hours on a plane with a two and three year old last month. And it was actually pretty easy! Claire and Maggie brought these Skip Hop backpacks filled with the following:
1. Books. I bought a set of eight Disney Princess Golden Books at Costco for $6. That way, they both had a new book for each leg of our trips. I normally don't allow movie character books into our home, so they were very exciting. These are pretty long, but managed to hold Maggie's attention because of the special subject matter. They each had three picture books from home in their backpacks as well, carefully chosen to interest them both (Little Critter, Robert Munsch, etc).
2. We always read books when the plane was taking off, because you have to leave the tray tables up. Then we pulled out the coloring books, blank notebooks, stickers, and crayons. Triangular crayons are awesome because they don't roll off the table.
3. Water Wow. We have four of these notebooks - animals, vehicles, fairy tales and make-up. Apparently they now have a bible stories one? They got one in their backpack on the way there and a new one on the way back. I'd have them color theirs, move onto another activity for a bit while it dried, and then switch.
4. Play dough. We prefer the Rose Art mini four-pack you can often find at the Target Dollar Spot because the lids are animal stencils. Built-in entertainment. I also packed some matchbox cars, so they could make roads and hills to drive on.
5. Wind-up toys. We have four - a waddling penguin, creeping caterpillar, and two flipping foxes. I've found them all at local toy stores. I'm pretty much always on the look-out for items that would make good airplane surprises. Watching these move across the tray table is surprisingly entertaining!
6. Travel magnetic drawing board. Ours are actually Crayola brand from the Target Dollar Spot. Another really good thing to pull out during take-off or landing because it doesn't require the tray table.
7. Bonus Items: Wiki Stix and Spot It Jr. I didn't pack these but we picked them up on the trip and they were great additions to our entertainment stash. When we visited Nashville, my friend Abigail gave us the Wiki Stix for the flight home. The girls loved the novelty factor and immediately set out creating rainbows. Spot It was the kids' toy of the moment at Chick-fil-A, where we ate during both of our trips, so we acquired a camping set and an animals set.
Once we'd worked our way through all of these items, at least two hours had passed. Then it was time for a meal, a bathroom break, and a movie for the second half of the flight. I can't believe I actually got to read a book while traveling with small children!
P.S. For our trip to West Virginia, we packed all our clothes (four people, five days) in one large suitcase. We bought this duffle bag to hold our pack-n-play, toddler air mattress, their bedding, and diapers. We also have these car seat bags (we always check our car seats) and this stroller bag, which fit our Baby Jogger City Select double stroller perfectly. West Virginia was the first plane trip we've ever done with our double stroller for (usually we go the single stroller + ergo route). Since we had quite long layovers, it was nice to have them both stroller napping in the airport. Of course, the stroller and the rest of our luggage just barely fit into our rental car, even though we upgraded to a 5-passenger SUV.