Yeah, travelling. I've done that.
I don't know how to be less straight forward, but do you have to go?
It might all go well with no prob, but it might not be easy.
My LO sleeps in the car, and the long drive was quite ok (we drove 10h in one day). Saying that, there was not much EAS on that day, I fed him in the car even if it wasn't quite time yet, because I knew it will help him sleep. A shield on the window also helps (the one that sticks if you know which one I mean), but it was a bit sunny where we drove. Oh yeah, and we stopped every couple of hours, got some fresh air, changed him, walked a bit around with him.
But a flight - don't go there. I won't do it again till he is 18 at least.
Regarding the swaddle, I think if it's working for you don't stop. Touchy babies need a bit longer than other babies to be weaned from it. You will know when it's time.