1Heat oven to 400°F. In large bowl, mix flour, 1/2 cup powdered sugar, 1 1/2 teaspoons cinnamon and the salt. Cut in butter, using pastry blender or fork, until mixture looks like coarse crumbs. Stir in chocolate chips and vanilla (mixture will be crumbly).
2Using hands, shape dough into 1-inch balls. On ungreased cookie sheets, place balls 1 inch apart.
3Bake 6 to 8 minutes or until set but not brown. Immediately remove from cookie sheets to cooling racks. Cool slightly, about 20 minutes.
4In small bowl, stir together 1/2 cup powdered sugar and 1 teaspoon cinnamon. Roll cookies in sugar mixture, shaking off excess back into bowl. Cool completely, about 30 minutes.