Preheat oven to 350°.
Cream together the butter and sugar.
Add in the egg and vanilla. Mix until well combined.
Add the flour and baking powder. Mix thoroughly.
Roll the dough out until 1/4 to 1/2 inch thick. Use a round cookie cutter to cut out circles. Transfer to an ungreased pan.
Bake at 350° for 6-8 minutes. Pull out of the oven when the cookies are puffy and no longer glossy.
Transfer to a wire rack and allow to cool completely.
While the cookies are cooling, microwave the caramels and milk for 1 minute. Stir at the 30 second mark. Stir until smooth and creamy.
Carefully spoon a few teaspoons of caramel onto each cookie, spreading until it almost covers the cookie.
Placethe cookies and caramel into the fridge for 10 -15 minutes or until completely cold.
Melt the chocolate chips for 30 second intervals until completely melted and incorporated.
Spread a small amount of chocolate onto each cookie. Let the chocolate layer cool and set up before serving.