Add 10 Oreo cookies to a food processor (or place in a zip top bag and use a rolling pin to crush) and pulse until the Oreos are a medium/fine crumb. Place in a medium size bowl and set aside.
Now add 15 Oreo cookies to the food processor and pulse until coarsely chopped. You want some big chunks. (You can also just chop the Oreos with a knife, or place them in a zip top bag and use a rolling pin to break them into coarse pieces).
Using an electric mixer, or a stand mixer fitted with the whisk attachment, whip the heavy cream and vanilla until stiff peaks form. About 2-3 minutes. *
Add the sweetened condensed milk to the whipped cream. Fold to combine.
Add the mini chocolate chips, crushed Oreos, and chopped Oreos to the mixture. Stir to combine.
Pour the "ice cream" mixture into a freezer safe container. I use a bread pan because it fits the contents perfectly! Top with additional Oreos and mini chocolate chips if desired. Cover with plastic wrap and aluminum foil.
Freeze overnight or for 6 hours.
*I freeze my metal bowl and whisk attachment 15-20 prior to whipping the cream.