When I studied Russian in college, we were taught that, generally speaking, one used в with "enclosed spaces" and на with "open spaces", which may be a better guideline than trying to say that one equals "in(to)" and the other equals "on(to)". This is also true for their antonyms: the preposition из suggests leaving an "enclosed space" while с suggests leaving an "open space."

Admittedly, in practice it may not be always obvious which is an "enclosed space" and which is an "open space." For example, if I'm not mistaken, the noun аэропорт was historically considered an "open space" (think of the runways) and therefore usually took на, but nowadays the word is seen more as an "enclosed space" (think of the terminal buildings) and thus the preposition в is often preferred.