Add the ice cream, milk and chopped pineapple to a blender. Puree until smooth. Pour into the popsicle molds and freeze for 20 minutes.
Rinse the blender pitcher out and then add the ice cream, milk and chopped strawberries to a blender. Puree until smooth. Pour into the popsicle molds over top of the semi-frozen pineapple layer and freeze for another 20 minutes.
Rinse the blender pitcher out and then add the ice cream, milk and chopped banana to a blender. Puree until smooth. Pour into the popsicle molds over top of the semi-frozen strawberry layer. Sprinkle mini chocolate chips over top, if desired. Freeze for at least another 2-3 hours or until frozen solid.
To easily remove the yogurt pops from the molds, run each one in the mold under hot water for 5-10 seconds and then gently slide out.
Keep any remaining yogurt pops in the freezer for up to one month.