Place the crushed Oreos in a bowl and set aside. In a separate large bowl, beat the cream cheese until smooth.
Add the peanut butter, powdered sugar, and milk to the cream cheese. Beat until the mixture is fully combined and creamy.
Fold 1 cup of whipped topping into the peanut butter mixture until it becomes light and uniform.
In a trifle dish or four individual glasses, begin layering by spooning a layer of crushed Oreos on the bottom.
Add a layer of the peanut butter mixture over the Oreos, followed by a thin drizzle of melted chocolate chips.
Repeat the layers once more, ending with a final layer of the remaining whipped topping.
Sprinkle a few extra crushed Oreos on top and drizzle with any remaining melted chocolate chips before serving.