We've flown quite a few times with our daughter, who's now 3 1/2.
Here are my tips:
- Others have suggested a DVD player-- I'd second that! Make sure it's fully charged and if available, get a second battery. I've had flights delayed and was able to play a movie for a bunch of the other kids waiting too.
- Fruit by the foot snack. This seems to last longer than a bag of fruit snacks for chewing during take off. It's a novel treat for my daughter, and we reserve it for flights.
- New toy/coloring book/stickers/flash cards. Something small and easy to put away.
- Paper and Tape-- double stick, masking, patterned. My daughter likes to play with any type of tape.
- Pipe cleaners-- or "Cleaner Pipers" as my daughter calls them
- Car seat-- I'm an advocate for the car seat, even if it's only used on the plane. The one time I flew without it was the most horrible flight ever! My daughter was able to easily unlatch the airplan lap belt and I had a hard time keeping her in her seat. She wasn't able to nap b/c she did't fit well in the seat, and with the leather seats, she kept on slipping. She always sleeps while in her carseat and she does not try to get out.
- Re: Car Seat- I will sometimes have my husband preboard and set up the carseat and take on as many of the carry-on as possible. I wait until the final rows are called and then gate check my stroller. That cuts down the amount of time we're on the plane and checking my stroller late usually means it's the first one out.
- I pack one bag of all these things just for her, so I don't have to fumble through all the other carry on.
- A filled sippy cup or a juice box is allowed on-board for a baby/small child. We flew right after the new restrictions were in place and had no problems bringing them on. We didn't have to buy it after the security check.
- I talk to my daughter about the flight and she helps pack the bag of goodies. She looks forward to the different activities packed away. I always leave the new items as surprises.
Our flights are generally easy and not too painful. We also like flying JetBlue since they have free DirectTV. Since flying JetBlue, we haven't actually needed the DVD player on board, but we take it anyway for the hotel and airport.
Good luck!