Pour coffee, milk, pancake syrup, chocolate chips, and ice into the blender.
Blend until smooth, pausing to clean the sides of the blender and stir with a spatula.
While it’s blending, crush the Oreos into small pieces.
In a large glass, drizzle some chocolate syrup in the bottom of the cup, and top with a layer of whipped cream.
Sprinkle about half of the Oreos on top the whipped cream.
Next, pour the contents of the blender on top of the Oreos, and do not stir.
Top the drink with the remaining Oreos, whipped cream, and a drizzle of chocolate syrup. Enjoy!