In Pilotwings, the player attempts to earn pilot licenses through lessons in light plane flight, hang gliding, skydiving, and the use of a rocket belt.

To increase the realism of the game's flight simulation, the developers extensively utilized the SNES's Mode 7 capability, which mimics 3D graphics by rotating and scaling flat objects.

In each event, the player controls one of four aerial vehicles and must complete a task (usually flying through floating markers) then land safely and accurately within a time limit.

[5] In the skydiving, rocket belt, and hang glider modes, landing on moving platforms rewards players with a perfect score, and a bonus stage for extra points may be earned by falling into the water of a target area.

[10] The player must fly an attack helicopter from an offshore aircraft carrier and retrieve the captives by landing on a helipad on the island.

[4] As the player flies over the island, they must successfully dodge anti-aircraft fire from ground-based turrets which are able to shoot down the helicopter and end the game with a single hit.

[2][1][13] The game's musical score was composed by Soyo Oka, while her superior Koji Kondo was responsible for the sound programming and the helicopter theme.

[17] A flight simulator game resembling Pilotwings called Dragonfly was shown during the official unveiling of the SNES to the Japanese press on November 21, 1988.

[26][30] Pilotwings was generally seen as a showpiece title for the Super NES, demonstrating its Mode 7 features, built-in sprite scaling, and high-end sound chip in a conspicuous manner.

[35] Its level of challenge was also positively noted; Mean Machines found that practicing the flight tests and reaching the end of the game was very rewarding.

[30] Official Nintendo Magazine remarked in 2009, "This early SNES title is still enjoyable enough to be considered a true classic.

However, an anonymous blogger claimed in late 2009 that Factor 5 had indeed finished working on it, but that Nintendo was not confident in publishing it.

[59] In 2023 Roger Waters made reference to the game in a narrative dream sequence involving a battle of good versus evil in On The Run, the 3rd track of The Dark Side of the Moon Redux A stage based on Pilotwings makes an appearance in Super Smash Bros. for Wii U and Super Smash Bros.