Set in the Pampas of South America, a little gaucho prepares to go hunting all alone. Attempting to hunt for condors in the mountains, the gaucho then discovers a nearby nest in the tallest mountains. All he found was an unusual winged burro in which he thought it was a condor. Gauchito then prepares to capture the flying burro but it manages to escape. Unhappy for his unsuccessful plan in capturing the burro, he tries to distract him into eating his hat to trick him until he jumps on him to ride on the burro like a cowboy. After riding on it, Gauchito decides to train the little burro as he planned to win thousands of pesos to be rich. By training him, the little burro learned new tricks and became best friends with Gauchito.
The next day, Gauchito and his tamed burro watch a festival of gauchos in which Gauchito started thinking of something bigger to become richer. Gauchito started thinking he would win 1,000 pesos for winning a racing competition. Attending the great race, Gauchito whispers to Burrito's ears to remember the abilities he used when he rode on him and trained him. As the race begins, Gauchito is left behind while the other gauchos are competing for the grand prize as Gauchito grabs his knife that he packed and cuts the rope in order for Burrito, the winged burro, to use his wings in order for him to fly. Upon riding on him, Burrito flies in a very fast speed, passes the other gauchos, and wins the race. Upon winning the bag of pesos, Burrito flies away with Gauchito holding his leash, not taking the prize with him after the race, ending the segment.
- The Flying Gauchito was originally planned for inclusion in Saludos Amigos, but was shelved in favor of El Gaucho Goofy serving as Argentina's representation in the film.
- A sequel short, The Laughing Gauchito, was briefly in production before being cancelled. A reconstruction was featured on the Laserdisc release of The Three Caballeros.