Place freezer-safe container (like a 9×5 loaf pan) in the freezer for at least 15 minutes.

While container is chilling, use a stand mixer or hand mixer to whip cold heavy whipping cream into stiff peaks (stiff whipped cream). This will take a few minutes.

Use a spatula to fold in sweetened condensed milk and vanilla extract.

In a Ziploc bag, add 12 Oreos and 12 chocolate chip cookies. Seal bag and use the bottom of a water glass to smash and crush cookies into desired-sized pieces.

Open bag, and empty cookie pieces into mixing bowl. Fold in cookies using a spatula.

Place mixture into the chilled, freezer-safe container.

Break apart extra 4 cookies and place on top.

Cover container with plastic wrap, and slide container into a gallon Ziploc bag.

Place in the freezer for at least 12 hours (24 hours is ideal). Ice cream stays fresh in the freezer, covered, for 1 month!