Preheat oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats.
In a medium bowl, whisk together flour, baking soda, cinnamon, and salt for 30 seconds. Add oats and stir to combine.
In a large bowl, beat softened butter, brown sugar, and granulated sugar together for 2-3 minutes until light and fluffy.
Add eggs one at a time, stirring vigorously after each until fully incorporated. Stir in vanilla extract until evenly distributed.
Add half the dry ingredients to the wet mixture and stir just until flour streaks disappear. Add remaining half and stir until just combined, being careful not to overmix.
Fold in chocolate chips using broad strokes until evenly distributed throughout the dough.
Scoop 2-tablespoon portions of dough and roll into smooth balls. Place on prepared baking sheets, spacing 2-3 inches apart (8-12 cookies per sheet).
Bake on center rack for 10-12 minutes until edges are golden brown and set but centers still look slightly underdone and puffy.
Remove from oven and let cookies cool on baking sheet for 5 minutes. Transfer to a wire cooling rack and cool completely for 15-20 minutes before storing.