Well, the jury is out on that. If you can drive something delicate at resonance, you can break it, most likely.
Easiest way to break a glass window, though, I suspect, would be to get a huge subwoofer, and drive it in feedback from accilerometer in the middle of the window.
That 21" woofer from B&C ought to suffice, if you have a 220 circuit to power the amplifier for it
This is kinda not in the headphone range, though.