Whisk together milk and pudding mix in medium-size bowl for 2 minutes. Fold in cookie chunks. Pour into ice pop mold and cover.
Gently insert ice pop sticks into mold, keeping as upright as possible. Freeze 6 hours or overnight.
Remove cover. Run outside of mold under warm water and gently pry pops from mold. Place in freezer-safe resealable plastic bag and store in freezer until serving.