Enter the Chiquita $5,000 Sweepstakes! THe Chiquita Sing Off gives you the chance to win $5,000 cash. The Chiquita Jingle has been a part of American pop culture for more than 70 years, and Chiquita is looking for the next Chiquita Sing Off star. Fans can enter the Sing Off contest for a chance to win $5,000! Must be 13 years or older to qualify. Hurry, this sweepstakes won’t last long.