Without giving too much away about the plot, eventually you'll be asked to buy the abandoned airstrip in the Las Venturas desert. Once you do, a mission will be available there, that makes you take flying lessons. After about five or six, you'll get your license. The parachute comes as standard in every plane, you don't need to buy it elsewhere.
Note, that some planes are easier to fly than others. The planes that you take your lessons in are a lot harder to fly than most, so don't despair about flying.
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Game Status:
[PS2]: N/A
[XBox]: N/A
[GC]: N/A
[PC]: N/A
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