J just turned 2 when we flew to Naples, Fl for a friends wedding. We went ahead and purchased him a seat ( best thing I did! ). Car seat was snug and he felt safe!
We brought just the small umbrella type stroller w/ us and they checked it before we stepped foot on the plane. Then when we arrived it was right outside the plane door.
Doc said the benedryl can make some kids hyper so we didn't even try that route. He was perfect the entire flight! And from experience, don't forget diapers/wipes/change of clothes for you both!
Ditto this. Sometimes Benedryl has the opposite effect on children and can make them hyper. Even so, Benedryl isn't recommended for a child that age. Definitely check with the pediatrician on this.
Plenty of snacks, books, and small toys. Do you have a portable DVD player?
If you haven't already checked the TSA site: TSA: Traveling with Children
Feeding the baby at take off and landing is a good idea to help with the pressure on the ears.
Check the stroller and the seat at the gate. They make travel bags for them if you're worried about damage.