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Yes, it' correct.
Also it can be said as "влетела В окно".

Welll, it is not correct.
"На-лететь" is not very close to "за-лететь" (and it's not the same as 'на-летать').
Well, it's perfect...

Not exactly, but near it.
First of all in russian we have 'он перешёл черту' in the same meaning as english "cross the line" idiom. "Пере-" as "over-" in "overpass".
But prefix "за-" produces...

> Also, If I had rewritten it as
> Он залетел 5000 миль.

It's wrong. "За-летел" implies crossing some border. For example "залетел на территорию", "залетел в ангар", "залетел так далеко как...