You know your baby. If he's happy in the mornings, that's probably the best time to fly. If he's good at napping on the road, then maybe nap-time is the ideal travel time. But if he needs to be in his crib to sleep, avoid booking your flight for that time of day -- you don't need us to tell you that a tired baby who can't sleep can get cranky!
Plan to arrive at the airport earlier than necessary. Getting to your gate -- even in smaller airports -- can be time-consuming, and you’re probably not going to make a successful mad dash to the gate with a child in tow. If you sail through security and have time to kill (yay, you!), find an empty gate area and let your toddler run free. This isn't the time to keep him quietly occupied in a seat with a book -- there's a whole flight for that!