Beat the softened cream cheese in a medium bowl until perfectly smooth.
Add powdered sugar and vanilla. Mix until creamy and well combined.
Splash in the milk, a little at a time, mixing until the dip is silky.
Fold in the whipped topping gently to keep the mixture light and fluffy.
Stir in the crushed cookies and mini chocolate chips until evenly speckled.
Spoon into a serving bowl and sprinkle with extra crushed cookies. Serve right away or chill briefly.