That depends on you and your child I think. I've heard red eyes are best with little kids because they fall asleep. But I don't want to bank on that and then have a miserable little person at midnight - would love to hear from other moms if that worked though.

We've flown a lot and what works best for us is to fly first thing in the morning. My daughter, now 3, has always been an early riser so getting to the airport for a 7:30 or 8 a.m. flight is not that big of a deal for us and those are the flights we look for. She's also in her best mood then. But if we couldn't get that, our rule basically has been not to schedule flights during her normal nap time or bed time.

Once you're on the plane, bring lots of snacks and new toys. We recently flew to Alaska - three flights, 12 hours of travel. I got a bunch of toys and books from consignment sales and wrapped them in the comics section from the Sunday paper. So, not only did she have new things to play with, we killed time unwrapping the stuff and reading the comics (your guy might not be ready for the reading yet, but he'd love the unwrapping.)

WARNING: This can backfire on you because my DD later complained when something I pulled out of my bag was not wrapped.

Good luck!!

Sarah