This flight simulator for the SNES features 4 training locales and instructors with 4 flight mechanisms to master. It also features a helicopter rescue mission as an added bonus. The 4 main flight mechanics include the Light Plane, Skydiving, Rocket Belt, and the Hang Glider. With the inclusion of the game's Expert mode there is a total of 8 training levels and 2 rescue missions.

When it was originally released Pilotwings wowed the world with mode 7 graphics which allowed for hardware scaling and rotation. In terms of gameplay, this system feature allowed some of the very first open ended 3D environments to be explored. Although the pseudo-3D effects featured in Pilotwings would be dismissed as primitive by most gamers today, they can still effectively put a pit in a player's stomach.