Preheat oven to 400 degrees. Prepare two baking sheets by lining with parchment paper. Set aside.
Add flour, ½ cup of powdered sugar, 1½ teaspoon ground cinnamon, and salt together in a food processor. Pulse a few times to combine. Cut butter into cubes and add to food processor with vanilla extract. Pulse until butter turns into crumbs. Toss mixture with mini chocolate chips.
Using your hands, grab about 1 tablespoon of mixture and press crumbs into a ball. The heat from your hands will help melt the butter slightly so it will take shape. Place ball on prepared baking sheet. Repeat with rest of the dough, placing dough balls no more than 1 inch apart. These cookies won't spread much so no need to keep them very separated. Chill them in the freezer for 10 minutes.
Bake in preheated oven for 7-8 minutes or until the edges begin to brown. Remove from oven and let cool for 15 minutes. Place remaining powdered sugar and cinnamon in a small bowl. Toss cookies in powdered sugar twice. Serve immediately, or let them cool and then store for up to 3 days.