Pilot Academy is a flight simulator on the PSP which encompasses all eras of flight, ranging from historic WWI fighter planes such as the famous Fokker Triplane (flown by the "Red Baron" Manfred von Richthofen) to modern military and civilian jet aircraft like the F-15, F-16 and Boeing 747. All aircraft names and designs are licensed.

In the initial lessons, the game teaches the player the basics of powered flight for both civilian and military purposes. The game uses all PSP buttons to deliver a flight simulation feel with the analog nub serving as a joystick. Controlling the flaps, air brakes, raising and lowering the landing gear as well as using the tail rudder are also possible. Military aircraft feature air-to-ground missiles, air-to-air-missiles, a machine gun and flares for self defense against missiles. The only thing missing from the simulation is a fuel gauge, but since most missions are rather short, this was probably a deliberate design choice.

After civilian and military flight lessons are completed, the player is free to choose from various missions and challenges. Completing a task successfully unlocks new aircraft in the player's hangar which can then be flown any time in free flight mode (but only on the tropical map). Distinctions are also awarded for completion of a mission based on time taken, aircraft integrity, completion of objectives and level of excitement/comfort of passengers (if any) and determine the level of proficiency of the player pilot.

Flights take place over different types of terrain including tropical, desert, snow covered mountains and canyons and in varying weather conditions like rain, snow and even in a storm. Some missions begin while already airborne, while others require the player to taxi onto the runway, takeoff and land after completing the objective.

Multiplayer supports up to four players dogfighting against each other or cooperatively with planes from any of the four military eras, e.g. a dogfight between a WWII propeller plane like the P-51 Mustang or the Spitfire versus an F-14 Tomcat or F-16 Falcon is possible.