Hi S., Sorry for taking so long to respond - I hope this reaches you in time. I used to fly A LOT with my first, but the most significant flights were when I flew on 2 seperate occasions to Hawaii. First with my 2-1/2 yr old years ago (husband stayed home), then in April with my 11 mo. old & 6 yr old (again, husband stayed home and I met my family out there). I tried giving her Benadryl (ok'd by pediatrician, but you should probably check with yours) because so many advised me to us it, but it didn't seem to affect my child. I carried a bottle of milk and sippie-cup of milk, and kept it cold by freezing bottles of water, which when thawed, became drinking water for me. At the time, I was breastfeeding. I planned it so that I were nursing her upon takeoff (I learned if you start too early while the plane is still taxi-ing, the baby finishes before actual liftoff, so I've timed it better now to start right before we take off). And I nursed her upon descension. The suckling helps keep her ears equalized as the pressure changes. This works with bottle/sippie cup as well. Here's something to keep in mind. While they give you minimum snacks on board, pack enough snacks/drinks/diapers/wipees just in case you get stuck on plane for 18 hrs as contingency. This likely won't happen, but it has happened, and it's good to be prepared. I also carried the infants' tylenol/motrin just in case. I brought crayons/paper, books, her favorite toys that were small enough and not too loud, a laptop that plays DVD movies, and a blanket. Always have 1 or 2 change of clothes for baby, and it isn't a bad idea for yourself, too. It came in handy for me on my 1st trip to Hawaii, when my daughter spilled juice all over my lap. My umbrella stroller has been handy for transporting her through airport, but they're required to be checked in (via gate-check is recommended) I also brought carseat and did gate-check for that, too if you child doesn't have own seat. Good luck!