Preheat oven to 350°F. Line baking sheet with parchment paper and set aside.
In a medium bowl, whisk together flour, baking soda, salt and pumpkin pie spice and set aside.
Using a stand or electric mixer in a separate bowl, beat the butter and sugar on high speed until light and creamy, at least 3 minutes. Do not skip this step. Once combined, add the pumpkin spice pudding mix, eggs, pumpkin pure and vanilla and beat on high for 2-3 additional minutes.
Slowly add half of the dry ingredients to the wet ingredients and turn the mixer on low to start so the flour doesn't get everywhere. Turn the mixer up to high and mix until combined. Add the rest of the dry ingredients and repeat until dough is just combined. Add chocolate chips and stir with a rubber spatula until incorporated.
Drop cookies by ¼ cup onto the prepared baking sheet. Bake for 10-12 minutes, or until slightly golden and just set on the top. Allow to cool on the baking sheet for two minutes then transfer to a baking rack to cool completely. Place baked cookies an air tight container in the refrigerator for 3-5 days or in the freezer for up to 3 months.