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Preheat oven to 350°F and line a 12-count cupcake tin with paper liners (or spray with nonstick spray). Set aside.
Combine the flour, baking powder, and salt in a large bowl.
In a separate large bowl, using a hand or stand mixer fitted with the paddle attachment, beat the sugar and vegetable oil until light and frothy.
Add in the milk, eggs, and vanilla, and beat until smooth and foamy.
Add the dry ingredients to the wet ingredients in 3 increments, beating until smooth after each addition. Fold in the chocolate chips.
Divide the batter evenly between the lined wells of the cupcake tin.
Bake the cupcakes in the preheated oven until the tops become a light brown color, about 18-20 minutes.
Let cool for 5-10 minutes in the pan, then transfer the cupcakes to a wire rack to cool completely.
While the cupcakes are baking, use a hand or stand mixer fitted with the whisk attachment to beat the butter until smooth and creamy.
Add in the powdered sugar, a little at a time, until fully incorporated. Then, add in the vanilla and milk, and mix until combined.
Once the cupcakes have completely cooled, pipe the icing onto the cupcakes.
Place a few chocolate chips and a mini chocolate chip cookie onto the piped icing, if desired.