Preheat oven to 400 F degrees. Line a baking sheet with a silpat or parchment paper.
In a large bowl, combine the four, sugar, cinnamon, baking powder and salt. Whisk together.
Add cold butter. Using a pastry cutter or two forks, cut butter into flour mixture, until butter is broken up into small pieces the size of large peas. The mixture should look sandy.
In a small bowl combine vanilla extract and milk. Pour mixture into dry ingredients.
Combine until the dough starts to come together and pull away from sides of bowl. Add in chocolate chips, stir until combined.
Pat dough into a large disc about 3/4 inch thick on a lightly floured surface. Cut disc into 8 wedges. Place wedges on prepared baking sheet.
Bake for 15-17 minutes, until the scones are lightly browned. Transfer scones to a wire rack to cool.
Once the scones are cooled make the glaze: In a small bowl, add powered sugar, cinnamon, vanilla extract, and 1 tablespoon milk. Mix until glaze becomes a smooth, pourable consistency. Add additional milk a teaspoon at a time to thin glaze as needed.
Drizzle glaze over cooled scones. Allow glaze to set before serving.