Preheat the oven to 350°F. Line a cupcake pan with cupcake liners.
In a large mixing bowl, combine the sugar, vegetable oil, eggs and vanilla extract. Beat on medium speed until the eggs and oil are well incorporated and the batter is lighter in color, about 2 minutes. Scrape down the bowl as needed.
Next mix in the sour cream and beat until well combined.
Add half the flour followed by the baking powder and salt and beat on low speed while pouring in half of the milk and mix just until the flour starts to incorporate.
Finally add the remaining flour, mixing on low speed while pouring in the remaining milk and beating until all of the ingredients are well combined.
Use a spatula to scrape down the sides of the bowl and stir the batter from the bottom to the top to ensure it’s well mixed
In a large Ziploc bag, crushed the chocolate chip cookies into small pieces using a rolling pin or something similar. Fold the crushed cookies into the cupcake batter.
Using a large cookie scoop, divide the batter evenly, filling each liner ⅔ full. Careful not to overfill.
Bake at 350°F for 18-22 minutes. Test the cupcakes for doneness by inserting a toothpick into the center of the cupcake. If the toothpick comes out clean, the cupcakes are done. Cool completely.