Whisk together flour and salt. Set aside.
Beat butter on medium-high speed with an electric mixer until smooth and creamy. Add both sugars and vanilla extract, and mix until incorporated and fluffy. Add the flour mixture and milk, and mix well. Fold in the chocolate chips, and then the Cool Whip. (You'll probably get a good arm workout here.)
In whatever dish or cups you decide to serve this in, spoon or pipe a layer of cookie dough filling. Sprinkle with chopped cookies and drizzle with caramel sauce. Repeat the layers until your container is filled.
Cover and chill for 2-4 hours.