Question

If a planet entered a black hole would it crush the planet completely or in theory would chunks make it through?

Answer 1

It would be crush completely.
When a planet enters a black hole the first thing that happens is called spaghettification , the planet would stretch out like spaghetti, then it would be completely destroyed . Spaghettification doesn't take place everytime something enters the black hole , if this doesn't happen then the planet would be crush completely.

Answer 2

completely crush. theoretically a black hole has a indefinite density (or just immeasurable with our tech) and mass. Thus light and matter cannot escape the gravitational pull