Red Eye Flight With

I would take the overnight & hold hiim during the flight, I'm sure he'll feel secure enough to sleep. You may not sleep well, but I bet he will. Good luck, I just did this a few days ago. He slept well, I didn't, but it's all about them anyway....goodluck....here's a tip someone just told me about equilizing hte ear pressure on the way up & down...a lolipop (natural one of course). Have fun.

Just got back from a trip with my 18 month old. We tried to take the red eye, but there was a mechanical problem and it was rescheduled for 11am the next morning. There were lots of kids on the flight and it made it really hard for the parents. Couple of tips: My son sleeps mostly in his crib. He had a really hard time falling asleep on the plane. He had a really easy time walking around the airport for hours, which tired him out, but it took a lot to get him to fall asleep on the plane. Travel in a group! Don't try to do this alone. I traveled with my mom and husband, and it was still really trying. Going through security with bags, diaper bags, stroller, purse, and having to take off not only my shoes and jacket, but his shoes and jacket as well... it was hard. Leave plenty of time for snafoos and store up a lot of PATIENCE. Bring lots of things to entertain the baby on the flight. Books, magazines, toys, food, a water bottle (that you can fill up after going through security). Try your best to get your baby to run around the airport, then change and feed him and make him as comfortable as possible on the plane so that he can sleep. We made it through four flights in four days and it was difficult at times, and easy at times.

Good luck!

YES!!
We took a 10mo old and 22 mo old to the philippines in 2005. mind you it is a 15 hour trip just on the first flight. we did it overnight and it is the best thing we ever did.
how big is your baby? some flights have basinets you can call ahead and reserve they come down from the wall right in front of your seat. that was a life saver even for our big 10 mo. old.
since you're only going 5 hours it will be much nicer to have him sleeping. he'll probably do fine sleeping on your chest or in the bassinet. it is totally worth the try.

Veteran traveler here. (We have traveled back East to visit relatives twice a year since my oldest, now 12, was born. We have three.)

I say don't do it. Red Eye flights used to be wide open and you could easily sleep. Not any more they, like all other flights are jammed. Your little one might sleep in his car seat the whole way or he may stay awake the whole flight fussing. Imagine a plane full of sleepy travelers, you and a fussy toddler for 5 hours. Not a very pleasant thought.

Also, please, please,please make certain you are not intending to lap child your toddler. We tried it once on a very short, but completely full, flight with or oldest. He was a very easy child but the flight was a nightmare. Plus, it is just not safe.