really depends on the surface/make of the chalkboard.
if its a painted wood surface i would not offer any sort of life on the vinyls.
matt paint doesnt allow good adhesion and the vinyl often curls back over time. coupled by the constant wiping off of chalk with a cloth and its easy to catch the letters and add further damage.
that said, there are some cheap plastic type chalkboards with a semi gloss surface "when new". these should take the vinyl but ide heat them to allow the vinyl to take on the grain of the board.
its a bit like when you stick "even" a cast vinyl to the moulding or bumper of a car, it sticks fine but does come away eventually. often sooner rather than later.