As many times as the song requires.
I anticipated this would be said and inserted 'generally' into the title but it didn't stop you from saying it
The classics are the classics for a reason!
Seriously: it does depend on the song, for me.
Sometimes I open up the song with the chorus and, in those songs, there is generally one or two more repeats that in others.
So, in songs that start with the chorus, it's generally 4 or 5 times.
In songs that open with a verse, 3 or 4 times.
Unless I repeat the chorus as an outro, in which case there'll be another time or 2 in there.
And, it also depends how long the chorus is, itself. If's it's a 1-line refrain, then I tend to repeat it a bit more than if its a 3- or 4-line chorus with a pre-chorus and all that.
So, getting back to my initial post... as many times as the song requires.