In a blender, combine the vanilla ice cream, whole milk, and vanilla extract. Blend until smooth and creamy.
Divide the milkshake mixture evenly among the four tall glasses.
In a small bowl, layer the sliced strawberries on one side of each glass and the blueberries on the other side to create a patriotic effect.
Top each milkshake with a generous dollop of whipped cream.
Sprinkle red, white, and blue sprinkles over the whipped cream.
Insert a mini American flag toothpick into each milkshake for decoration.
Serve immediately and enjoy!