Preheat oven to 375° F. Line a baking sheet with parchment paper.
Combine pumpkin, granulated sugar, brown sugar, oil, milk and vanilla together in a mixing bowl with an electric mixer or stand mixer. Mix until well combined.
Whisk together the flour, baking soda, salt, cinnamon and pumpkin spice together in a separate bowl. Combine the dry ingredients with the wet ingredients and mix on low until combined. Stir in the chocolate chips. See photos above for a visual. The dough is pretty sticky, so I like to use a cookie scoop. Scoop the dough onto the parchment lined baking sheet, 2 inches apart, about 1 ½ - 2 Tablespoons in size.
Press the cookies down slightly with your fingers. Bake for 9-11 minutes until the tops are matte and the edges are set and they are cooked through.
Video
Notes
You can absolutely use milk chocolate chips instead of semi- sweet if you prefer a sweeter chocolate chip.
These are one of my absolute favorite cookies to freeze. The texture when they are frozen is so yummy. They make a great make ahead cookie or store-in-the-freezer cookie.
Make sure you use pumpkin puree and not pumpkin pie filling! This recipe is not designed to be made with pumpkin pie filling.