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Step 1
In a standing mixer fitted with a whisk attachment, beat the remaining 2 cups of heavy cream until soft peaks form. Add the powdered sugar, vanilla extract and salt and beat well. Set aside.
Step 2
Line the inside of a standard-sized loaf pan with plastic wrap on all sides. Working in layers and starting with the whipped cream mixture, spoon and spread the whipped cream, dunk the Chips Ahoy cookies in milk before laying out into an even layer, breaking the cookies up into small pieces to get them to completely fill in and cover the whipped cream. Drizzle a few heaping Tablespoons of Nutella over the cookies, using an offset spatula or a spoon to spread into an even layer.
Step 3
Repeat layers until your loaf pan is full, finishing with a layer of whipped cream. It’s completely up to you how much you spoon on each layer– if you want more whipped cream, do it! More chocolate, do it!
Step 4
Cover with plastic wrap and place in the freezer to set for at least 3 hours.
Step 5
When ready to serve, take the icebox cake out of the freezer. and lift out of the loaf pan, inverting the cake onto a serving dish.
Step 6
If desired, top with crumbled cookies. Use a hot, sharp knife to slice and serve! Enjoy.