C.J.
Hi A.,
In all honestly, there is no good time. You just have to pick your poison based on time you feel that you can handle it more. For instance, if you choose a flight early in the morning and you're tired and your patience are low, it's going to be twice as hard on the both of you! Pick what works for you with your schedule and you'll be able to better handle it. Bring your son's favorites (milk, snacks, juices, toys, comfort items, portable DVD player or iPod for his favorite music and shows) to keep him occupied. My son doesn't get to watch tv very often, so when I pull out the iPod Touch, he is glued to it, which helps in just getting thru the long travels, making it easier. Also, from my experience, having him in the carseat is the best option because it keeps him in place and also offers a source of comfort and stability as it is something that children grow accustomed to and rely on in car travel. Oh and if you are doing the carseat option, I highly recommend purchasing the 'Go Go Kidz Travelmate' - it is seriously worth its weight in gold for navigating the airports and air travel in general. Good Luck with your family travels!