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

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

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.