1. Combine pudding mix, chocolate chips and milk in a medium-size saucepan. Cook over medium heat, stirring, until mixture comes to a full boil, about 12 minutes. Cool 5 minutes.
2. Spoon 1 cup pudding in bottom of an 8-cup bowl. Top with 7 cookies. Spread cookies with 3/4 cup pudding. Layer with 1 cup cherries or raspberries. Top with 1 cup pudding and remaining 8 cookies. Spread with last 3/4 cup pudding and remaining 1 cup fruit.
3. Cover bowl. Refrigerate at least 6 hours or overnight. Remove from fridge and beat cream with sugar to medium-stiff peaks. Spread over pudding, leaving a small border at edge uncovered. Garnish with extra fruit. Serve chilled.