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Then youŽll get into a mission where you get to buy an old airport.
After you buyed it, you get into a new mission, where you have to lean to fly.
Then go up in the tower behind your Safehouse, step into the red marker that is in front of the TV, and then you get to the Pilot School.
Note: You have to clear 7-9 flying missions to make progess.
It will say when you clear the mission.