Most of the players take scheduled flights. In years past I've seen a number of players on our (Hawaiian) flights from the west coast to HNL for the Pro Bowl. Since it is individuals, and not whole teams going out for the game, there aren't any charters of large airliners for the players. I'm sure a few of the big $ players do charter Gulfstreams and the like to get there, but most of them go on scheduled airlines.
One smooth landing is skill. Two in a row is luck. Three in a row and someone is lying.