The critical time is when the plane first starts to descend. You'll feel your ears reverse the presssurization. Usually, if any passengers had problems, they were about an hour to 40 minutes out (longer for longer flights). They usually felt better at about 10,000ft.

Just be awake, which is not that hard since it's when you're getting ready to land anyway. Wish you had time to get your ears checked out. For your baby, one of the best, but not ideal ways to clear the ears is by crying. So if he's bothered, he'll cry and that will actually help (although best avoided, you'll at least know it's helping).

Remember that babies cry for a lot of reasons on airplanes. They're being jiggled around, they're too hot/cold, their schedule is messed up, etc. Don't assume it's the ears.

Since your baby isn't secure, you might want to feed anyway before landing, just so he doesn't need it when you're trying to get off the plane, get your bags, etc. I used to feed at that time, before placing them in the seats, just for that reason.

Bring some sort of pain killer for both of you. Take something about 1 1/2 hours before landing so it's at peak level when the plane starts to descend. Some sort of Advil/Ibuprofen might work better, since it has the anti-inflammatory properties that Tylenol lacks.

Get them checked out too. Make sure you don't have some sort of pesky problem that is easy to fix (which some ear problems are).

Good luck!