I've been meaning to draw Portal fanart for weeks but I couldn't decide what to draw.
Basically, this is my headcanon for how the whole series should ultimately end. Whatever GLaDOS says, her life is only going to be unbearably dull without Chell, and I rather think Chell would sort of miss her, too. Fate or chance will just keep throwing them up against each other until the day the entire Aperture Facility finally just collapses from exhaustion. And there's no way Chell can just let GLaDOS die and rot in there.
So they'll escape together.