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Yeah, they're water-tight, but if I fill mine up with air they're usually well-sealed enough to puff up with air. I've never tried putting the weight of my head on one though and I feel like at higher pressures (due to more weight resting on it) it won't stay air tight. A pillow that you have to reinflate 6 times through the night is more annoying than no pillow. Also it needs to be pretty sturdy to not pop, which would leave you pillow-less and with no dry bag for your clothes or whatever
The advantage of a dry-bag would be that it's dual purpose so doesn't waste weight/pack space, and you wouldn't have to blow it up with lung power, which I guess isn't that big a deal for a tiny pillow that's only about one lungful in volume anyway
I tried it just now with a Lomo bag I've got, it doesn't immediately deflate but who knows how long it'd retain air. I'd have to sleep on the floor to find out I suppose.
PS. general thread comment, big mistake that people often make with air pillows is over-inflating them I think, they're much more comfy when they're what I would describe as "half" full. Same for sleeping pads.
I also have one of these, by far the best part of my sleep kit in terms of weight/cost/pack size to comfort ratio.
Has anyone tried an empty dry-bag with air in it? Guessing it'd leak air in most cases?