Measure out your ice cream and prep your ingredients. To shave the semi sweet & milk chocolate bars (you only need a little piece of it, just about 1 square) use a rasp grater or you can chop the chocolate up finely with a knife.
Put all the ingredients into a blender and blend on high speed, slowly adding in the milk until thoroughly combined and smooth. Add a little extra milk if you like your milkshakes on the thinner side.
Pour into glasses, top with whipped cream and serve immediately!