Preheat the oven to 350°F. Coat two baking sheet with cooking spray or line with a silicone baking mat.
In a medium bowl, sift together the flour, cinnamon, baking soda and salt.
In a separate medium bowl, whisk together the oil, yogurt, pumpkin puree, granulated sugar, brown sugar and egg. Add the dry ingredients to the wet ingredients and stir to combine. Do not overmix. Fold in the oats and chocolate chips until evenly distributed.
Scoop 1 heaping tbsp of the dough and, using clean wet hands, roll into a ball and place on the prepared baking sheet, leaving 1 inch between cookies. Repeat with the remaining dough to make a total of 16 cookies. Using clean wet hands, slightly press down on each cookie.
Bake until a tester inserted into a cookie or two comes out clean, 14 to 16 minutes. Remove the baking sheet from the oven and transfer the cookies to a wire rack. Let cool for 10 minutes before eating.