Sometimes the airlines chess app gives you the option to play another passenger, but even after waiting for half an hour I've never been hooked up with another player. Has anyone else been able to?

Yes, as someone who is usually flying with my GF, I love this feature! Unfortunately air canada's implementation is abysmal and anytime there is a pilot announcement it interrupts the game long enough to break the network connection and cause it to end the game.

The best part about this is sneaking a look at your opponents screen if you are lucky enough to sit behind them.

It only works with passengers on your same flight. In practice, it's good for kids in the same family or school group who are sitting across the aisle from each other. I've used it for some of their other games

one flight I was on had trivia which allowed multiplayer. We ended up with about 10 playing the game. I thought it was a good idea for a networked computer and captive audience.

Some day we might fly on the same airplane!