Add everything to a blender:
Pour in the milk, ice, vanilla ice cream, vanilla extract, sugar, chocolate syrup, and 6 Oreo cookies.
Blend until smooth:
Blend on high for about 30–45 seconds until creamy and all the cookie bits are fully blended. If it's too thick, add a splash more milk.
Taste test:
Check sweetness and thickness. Want it sweeter? Add a little more sugar. Want it thicker? Add more ice.
Serve & top it:
Pour into two tall cups. Top with whipped cream, crushed cookies, and chocolate syrup drizzle if you'd like.
Enjoy immediately:
Serve with a wide straw or spoon and sip while it’s cold and dreamy.