Beat whipping cream with an electric mixer until stiff peaks form.
Add in 1/2 cup of powdered sugar and vanilla extract, mixing until combined.
Place whipped cream into another bowl, reserving about 1 1/2 cups for garnish.
Add cream cheese into mixer bowl with remaining 1/4 cup of powdered sugar. Mix at medium speed until creamy, about 2 minutes.
Add sweetened whipping cream and mix until combined.
Refrigerate while you make the cookie dough balls.
Roll cookie dough balls into bite size pieces, making at least 55 pieces.
Pipe or spoon cheesecake filling into serving dishes, about 1/3 full.
Layer about 5 cookie dough balls over filling in each dish.
Repeat with cheesecake, cookie dough and one more layer of cheesecake.
Pipe whipped cream over the top.
Crumble a bit of the cookie dough and mini chocolate chips for garnish.
Refrigerate for one hour or up to 24 hours before serving.