Preheat oven to 350°F and line baking sheets with parchment paper.
Whisk together flour, baking soda, salt, and cinnamon in a medium bowl and set aside.
Beat butter, brown sugar, and granulated sugar together until fluffy, about 3-4 minutes.
Add eggs, molasses, and vanilla extract to the butter mixture and beat until smooth and well combined.
Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined.
Fold in chocolate chips with a spatula until evenly distributed throughout the dough.
Scoop dough into rounded tablespoons and place 2 inches apart on prepared baking sheets.
Bake for 10-11 minutes until edges are set but centers appear slightly soft, then cool on pans for 5 minutes before transferring to wire racks.