Begin by placing your Oreo cookies into a sturdy plastic bag or a blender. Use a rolling pin or a pulsing motion on the blender to crush them gently but thoroughly.

Next, grab your blender and combine the crushed Oreos, vanilla ice cream, and whole milk. Blend on high until the mixture becomes smooth and creamy.

Once blended, take a moment to taste your milkshake. If you prefer it thicker, add a touch more ice cream; if you'd like it a bit thinner, pour in a splash more milk.

Carefully pour the creamy Oreo milkshake into chilled glasses, filling each about three-quarters full. Top each milkshake with whipped cream and drizzle chocolate syrup over the top.

Grab some straws or spoons and serve your deliciously refreshing Oreo milkshake immediately.