This tip, granted, might vary from child to child, but in general we've found that midday is best for us and many parents we know. Don't travel super early unless you are normally up at an unusually early time. Being up too early is the easiest way to lose something in the airport in addition to any semblance of sanity. We actually lost track of my wife's purse at the Burbank airport at 6AM - it got left near the check-in counter, complete with her only ID, keys, and wallet. We were lucky - it was still there when we raced back to look for it.
In our experience, the same applies for traveling late at night - unless you are all used to late hours, its probably best to avoid the late night flights if you have a choice. Between kids being at the end of their daily patience quotient and business travelers who are hoping to rest on the flight home, late at night can be a stress-filled extravaganza of frantic attempts to keep the babyheads quiet, mixed with visual balls of fire being hurled at you from multiple directions.
Of course, as I said, this one varies a little; but on our most recent trip, our toddler was too excited to sleep on our late night flight, which put him in a sleep deprived state for the next couple of days of the trip. However, he did nod off on the afternoon return flight, which surprised us. And when we think about it, this guideline has been generally true for us and a number of parents we know. Not to mention, when Jonah goes down for the evening, he HATES to be woken up to get off the plane, wait for luggage, etc., and he makes that painfully clear while we wait for an inexplicably long time for the door to open (can someone PLEASE invent a plane offloading system with more than one usable door?).
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