1. In a food processor, combine pineapple chunks, milk, and sugar; pulse until almost smooth, with some chunks of pineapple remaining.
2. 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.
3. 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).

Per serving: (per pop) 58 calories; 0.4 gram fat; 0.6 gram protein; 14.1 grams carbohydrates; 0.8 gram fiber
 
Note: To make chunks, peel, quarter, and core a small pineapple (about 1 pound). Cut into ¼-inch-thick slices, then cut into ¼-inch pieces.