I don’t think anyone can tell you which flight is best for you and your family. Some people swear by red-eyes because their child will sleep on the plane. That’s great, but what if I don’t. The only way I sleep on a plane is if I’m on some sort of sleeping pill, have an eye mask, neck pillow and ear plugs. It took me years of practice and a few long haul flights to finally be able to sleep on a plane. Of course as soon as I had gotten my sleeping system down, I got pregnant with my son. Even if we took a red-eye, I can’t very well take a sleeping pill. If he wakes up and needs something, I’d like to be somewhat conscious to deal with it.
So in general, whether we are flying to Philadelphia, Hong Kong or Maui, I prefer to take morning flights. I try to start the day as normally as possible, even if that means Dek goes to the airport in his pajamas, which he has done many times (yes, he is the child in the radioactive green or candy cane red striped pajamas that you can see a mile away). We have breakfast, get on the plane, take a nap, have some lunch, play, take another nap, and sometimes are off the plane in time to play some more, have dinner and go to bed. Then we can start the new day somewhat rested, depending on the jetlag, and ready to hit the ground walking at a moderate pace. Even if Dek is confused and cranky, at least I know where my head will be at so I can tackle anything Dek throws at me. Well, as much as I usually can.
As Dek gets older I may reassess this way of flying, but for now, I know as long as I take care of me, then I will be able to take care of him. So do what works best for you.
*I’m sorry I don’t have a more recent picture of Dek napping on a plane. Nowadays he is strapped to me in an ErgoBaby passed out. Hard for me to take a picture of that.