Preheat oven to 350 degrees F. Line 2 large cookie sheets with parchment paper. Set aside.
In a large bowl, add the flour, pumpkin pie spice, cinnamon, baking powder, baking soda, and salt. Whisk until sifted and combined. Set aside.
In a separate large bowl, add the granulated sugar, brown sugar, and vegetable oil. Beat with an electric hand-mixer until combined.
Beat in the egg, pumpkin puree and vanilla. Mix until just combined. Gradually mix in the flour mixture; just until combined. Try not to over-mix. Fold in milk chocolate chips.
Drop 2 Tablespoons of dough per cookie onto the prepared cookie sheets; spacing 2 inches apart. (15 cookies per sheet.) Bake for 12 minutes. Carefully remove from oven and let cookies cool right on cookie sheets.