We, too, have flown frequently with an infant and now toddler. Some tips we learned over the years have helped us tremendously. As an infant, you can bring warm breast milk/formula in a thermous for long flights. We flew to Hawaii when our daughter was 3 months old. Someone told us to do this and it made life much easier. A thermous keeps beverages warm for many hours and breastmilk/formula are approved liquids. It makes it easier in that you don't have to try and warm the formula yourself (very hard on a plane).
Also, for traveling with an infant on your lap, we purchased the Baby B'Air vest, which attaches to your seatbelt after takeoff (FAA approved after takeoff).
For a toddler, we travel with the Aquadoodle Travel Pad. It has a pen you fill with water (once past security) and they can 'color' without causing any damage. It is an inexpensive purchase and keeps a toddler busy as the water turns the page blue and then evaporates.
Finally, for ear popping, we carry a Gerber bottle topper, that can attach to any water bottle and turn it into a 'baby bottle' or sippy. It is an easy way for them to drink when in a pinch.
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