To make chunks, peel, quarter, and core a small pineapple (about 1 pound). Cut into 1/4-inch-thick slices, then cut into 1/4-inch pieces.
- 3 cups fresh pineapple chunks, (or one 14.5-ounce can chunks packed in juice, drained)
- 1/3 cup milk
- 1/4 cup sugar
In a food processor, combine pineapple chunks, milk, and sugar; pulse until almost smooth, with some chunks of pineapple remaining.
Pour half the mixture into a medium bowl (or a glass measuring cup for easy pouring). Pulse remaining mixture until completely smooth; add to mixture in bowl.
Divide evenly among eight 3-ounce molds or paper cups, and insert wooden sticks. Freeze until solid, at least 4 hours or up to 2 weeks (cover with plastic wrap).