Some information:
For those of you who don't know, the High Flyer Parachute Bag is a special limited-edition item that Rockstar added with the San Andreas Flight School Update. The parachute bag is a reward given to a player that completes The Flight School Event playlist. The event runs through August 22-24 (Refer to the Newswire post for more specific information about what else is included: [ Register or Signin to view external links. ] )

How to get it:
As mentioned above, the parachute bag is given as a free reward upon completing the event playlist. I'm still unsure if a player will get it when completing the playlist or by winning it since I won the playlist when I got mine.

EDIT: You can get the chute bag even if you lose the event. Thanks to Lazy Mofo for confirming.

The Playlist:
The playlist consists of 6 jobs varying from a capture mode to races to the new Acquire Targets and Air Force Zero modes that were added with the update.

The first job on the playlist is named Acquire Targets I which requires a minimum of 4 players to start. To briefly explain the job, you grab the "target" (which is essentially a red colored flag icon) and hold it for as long as possible. Whichever player/team is holding the target will gain points over time.

The second job is titled Under the Wing which requires a minimum of 3 players to start. This is basically a land race at the airport. Nothing more, nothing less. The race only allows players to use the stock Coquette Classic.

The third job is Air Force Zero I which is also a new mission added by Rockstar. The mission requires a minimum of 3 players to start. Air Force Zero is a 3 team game (technically 2) where there is an Attacking team, a Defending team and a separate team for only 1 person which is Air Force Zero. The lone player is going to use a Vestra fly to Paleto Bay. The Defending team defends Air Force Zero (obviously) while the Attacking team will try to destroy the Air Force Zero plane. Both the Attacking and Defending team are given Lazer jets to use. All other players except the player on the Air Force Zero team have unlimited lives. When the Air Force Zero plane is destroyed, the game ends.

The fourth job on the playlist is GTA: Airheads which is a capture job and requires a minimum of 2 players to start. The aim of the game is deliver 5 Besras to the base. One team spawns in Fort Zancudo while the other team spawns in the airport (note that the teams spawn in each other's bases.)

The fifth job is a parachuting job titled Take the Plunge. The mission requires a minimum of 1 player to start. It's a parachuting job, so it speaks for itself.

The sixth and final job is Flying Low which is an air race and requires 1 player to start. All players in the race are limited to Besra jets.

The reward:
The parachute bag is Light Green and Yellow with weed all over it (hence the name HIGH Flyer.)