Gather all your ingredients and tools.
In a blender, add the vanilla ice cream.
Pour in the milk.
Add the Oreo cookies to the blender.
Blend on high until smooth and creamy.
Check the consistency; add more milk if too thick.
Drizzle chocolate syrup inside the serving glasses.
Pour the milkshake into the prepared glasses.
Top with whipped cream and additional crushed Oreos.
Serve immediately with a straw and enjoy!