It could be interesting. I'm going on a trip soon and I plan on using my iphone to take a photo each place I take a photo with my SLR. When I get home and sync, I'll be able to use iPhoto and see all these places in the maps section. Then I can use that location info and add it to the photos I'll be taking with my big camera.
As far as on the flight, I think if you put your phone against the window and let it search, it just might lock onto the GPS. A lot of people seem to forget it's line of sight, so point it out the window. I even experience this in my car now and then. The cell towers will give me an approx location, and when I put my phone near a window, it will get the exact lock and show me the blue dot. You're right though, with no data service you'll be looking at a grid. Had that happen in the middle of the nowhere once. (though I placed a bookmark and was able to find it later on google maps when I got home)
Anyway, I'm hoping it'll work through the window, because I'd like to take a picture every 30 minutes or so and check out the locations later in iPhoto when I get back home!