Ok so jamaica will be fun. Look up the migraine x earplugs. They also make an airplanex one too. At first i hated them. But they do help with my migraine pressure pain. They are a bit uncomfortable so i will just put one in the ear where my migraines show up. But its almost immediate relief for me. And once you get there you get to relax and enjoy jamaica! Have a fabulous trip.

Thank you so much for your reply. I was worried about how the cabin pressure would affect my head pressure. My problem is that I do not know what triggered it. It has happened once before years ago but apparently, when they happen they tend to linger. I agree that whatever this is, I am not letting it stop me from enjoying life. I have a 90 minute flight to Dallas and then 3 hours to Jamaica. I will do all the things you suggested.

Yes for me it's better than a long car ride with the sun.
Take a sleep mask and headphones to listen to, for me classical music is relaxing.
I also pay the extra, it's not much, for the disability. You get through security faster and don't have to wait in a line. I even use the wheelchair because standing and walking that long is bad for me and besides uptick in migraine I might faint.
I have a disability card but they have never asked for it.
It still gets bad for me with all that so I can't go alone but like I said, better and faster than a car ride with the sun.

I always have my migraine medications wherever I go. Just like the American Express slogan.."Don't leave home without it."

I also include Miclizine (Dramamine) which I take as soon as I sense I have an episode of dizziness coming. I am prone to vertigo so I don't take any chances. I also try not to suddenly move my head to the left when turning as I noticed that sometimes I get vertigo with that movement.

My advice when traveling is, as soon as you have an aura or even just a little, tiny feeling of a headache coming, migraine or not, immediately address it before the headache will take control.

Have fun traveling. My family will be flying to Cancun in 2 weeks. Hope my migraine will stay in California and I enjoy my trip, migraine-free.