Preheat the oven to 400 F. Line a baking sheet with parchment paper.
In a food processor, combine and process flour, sugar, baking powder, and salt. Chop cold butter in small cubes, add to the food processor and process until the mixture resembles coarse meal. Add milk, and pulse a few times just until combined. Turn off the food processor, remove the blade, then, using spatula, fold in chocolate chips, avoiding to handle the dough too much.
Move the dough onto a lightly floured surface. With floured hands, divide the dough into 6 or 8 equal portions, and drop the dough in small flattened balls on the prepared baking sheet.
Bake the shortcakes for about 15-20 minutes, until the tops turn golden-brown. For decorating purposes, after 10 minutes of baking, remove the baking sheet from the oven and carefully place extra chocolate chips on top of each shortcake, lightly pressing the chips in so that they remain on top (which already gets crusty) and don't fall off - and then, return the baking sheet to the oven, and continue baking for the remaining amount of time.