Rogers and Tilly playing chess could be a red herring since it’s so obvious; however, there is a big chess motif in Through the Looking-Glass by Lewis Carroll.
Oh I know, I’m just suggesting that the writers were banking on that connection to make viewers (and probably even Rogers himself) come to that conclusion that Alice is Hook’s kid, but it’s actually a diversion for the real reveal. If so, then kudos to the writers for having been clever (#thingsIneverthoughtIdsayagain) in pulling off a bait and switch reveal.
If the specific chess piece had been a pawn, (the piece that Alice was considered to be throughout Through The Looking Glass) or a Queen, (which Alice became in the end of the story), then I’d be more inclined to think that the chess piece could be representing Alice. But this very specific piece that’s related to Hook’s kid is the piece that looks like a tower. A tower has nothing to do with Alice, and everything to do with Rapunzel.
The piece that Hook’s daughter kept was a knight, because he was her knight, and that fits with the Prince coming to visit Rapunzel in her tower like in the original story.
The fact that his daughter was imprisoned but he was still able to visit her every day in secret, there’s no Alice connection to that, but it fits for Rapunzel.
Basically, IMO there’s still more evidence that Hook’s daughter will end up being Rapunzel, and the chess connection to Alice is tenuous in comparison, so I remain unconvinced.