Preheat the oven to 325°F. Spray an 8-inch springform pan with baking spray and line the bottom with parchment paper.

Combine crushed chocolate chip cookies, melted butter, and sugar. Press half of the crust mixture into the bottom of the pan and the remainder around the sides. Bake for 10 minutes, then cool.

Beat together cream cheese, sugar, and vanilla extract until smooth. Add eggs one at a time, then mix in heavy cream. Split dulce de leche into two piping bags.

Pour half of the cheesecake batter into the crust. Drizzle dulce de leche over the batter and swirl with a knife. Top with the remaining batter and repeat the drizzle and swirl with dulce de leche.

Place a deep baking dish filled with warm water on the bottom oven rack. Place the cheesecake on the top rack and bake for 50-60 minutes, or until the edges are set and the center is slightly jiggly.

Turn off the oven and let the cheesecake cool inside for 60 minutes, then remove and cool further on the counter for 30 minutes. Refrigerate overnight.

For the whipped cream topping, beat heavy whipping cream, powdered sugar, and vanilla extract in a chilled bowl until stiff peaks form. Pipe around the cheesecake edges.

Soften the remaining dulce de leche and pipe a criss-cross pattern over the cheesecake before serving.