Prepare the frosting: In the bowl of a stand mixer, beat cream cheese, vanilla and powdered sugar together until well combined. Add milk and mix. Set aside.
Prepare the Cinnamon Swirl Mixture: Stir all ingredients together by hand or with a beater/mixer and add to disposable piping bag or plastic baggie with a small hole cut in the corner. Set aside.
Make the Batter: In a large bowl, combine flour, sugar, baking powder, baking soda, cinnamon, and salt and whisk together. In a medium bowl, combine remaining ingredients and mix well. Add wet ingredients to dry ingredients and stir just until combined.
Preheat a skillet to medium high heat.
Spray with cooking spray or rub with butter.
Pour the pancake batter onto the hot pan using a 1/4 cup measuring cup.
Let the pancakes cook for about one minute; they will start to set up just slightly. Then use the piping bag to gently swirl the cinnamon mixture into the pancakes, pushing slightly into the batter so the cinnamon mixture is swirled into the batter, not just on top of the pancake. Keep the swirl close to the center of the batter so the mixture doesn’t melt off the side of the pancakes.
Gently press 5-8 chocolate chips on top of the cinnamon swirl.
when the edges start to look done, use a wide spatula to flip the pancakes.
Cook for 3 to 5 minutes. Repeat with remaining batter.
Serve with the frosting.
*You will want to wipe your pan clean every few pancakes so you dont get burnt cinnamon on the bottoms of your pancake.