Preheat oven to 350°F; line baking sheets with parchment.
Whisk flour, baking soda, salt, and cinnamon in a medium bowl; set aside.
Beat butter and both sugars about 3-4 minutes, until fluffy.
Beat in eggs, molasses, and vanilla until smooth and well combined.
Gradually mix dry ingredients into wet on low just until combined.
Fold in chocolate chips evenly with a spatula.
Scoop rounded tablespoons onto prepared sheets, 2 inches apart.
Bake 10-11 minutes, until edges set and centers look slightly soft. Cool on pans 5 minutes; transfer to wire racks.