I am terrible at clearing pressure in my ears, have always been. It used to be that my hearing was affected for about a week after every flight, on top of the pain particularly on descent.

However, maybe ten years ago I started using Earplanes (also mentioned above), and they do wonders for me. My ears are still not entirely comfortable, and I do have some slight hearing issues for maybe 24 hours after flying (like for a bad cold, maybe), but that is it.

I also tried decongestant nasal spray, but that never did anything for my (in connection with flying).

If you doc says it is safe for you to do so, I'd definitely try the Earplanes. Maybe go somewhere not too far, where you can take the train home/drive, if need be?

DanishFlyer