Preheat oven to 350° F. Grease and flour 12 cups of two muffin tins.
In a medium bowl, whisk together flour, baking soda, salt, and cinnamon.
In a large bowl, using a hand mixer, beat the butter and sugars until smooth. Add the eggs and vanilla and beat until combined.
Slowly add the dry ingredients to the butter mixture, then add the melted chocolate chips and beat until combined.
Fill the prepared muffin cups 3/4 full and bake for 20-25 minutes, or until a toothpick inserted in the center of a cupcake comes out clean.
Cool cupcakes in the pan for 5 minutes, then transfer to a wire rack to cool completely.
To make the frosting, in a medium bowl, using a hand mixer, beat the butter and sugar until fluffy.
Add the whipped cream and milk and beat until well incorporated.
Fill a pastry bag with the frosting and pipe it onto cooled cupcakes.