Combine sugar and water in small saucepan over medium-high heat. Cook, stirring occasionally, until sugar melts and begins to bubble. Pour into 9-inch square glass baking dish; tilt pan to evenly coat bottom and sides with sugar. Tear 5 tortillas into bite-size pieces. Place evenly in baking dish. Sprinkle pineapple and 1/3 cup chocolate chips evenly over top. Tear remaining 5 tortillas; place evenly in baking dish. Sprinkle with remaining 1/3 cup chocolate chips. Whisk eggs, milk, and cinnamon in medium bowl. Pour over layered tortillas in baking dish. Cover surface with plastic wrap and press down lightly to distribute egg mixture over assembled tortillas. Set aside 30 minutes to allow egg mixture to soak into tortillas. Preheat oven to 350°F. Bake 53 to 55 minutes or until pudding is firm. Cool 10 to 15 minutes. Serve warm with whipped cream. Makes 8 servings.
Tip: For a Dulce de Leche version of this pudding, replace the chocolate chips with butterscotch chips.