Preheat waffle iron according to manufacturer's specifications and spray with non-stick cooking spray.
In a microwave safe bowl, add the chocolate chips and 1/2 cup milk. Microwave for 30 seconds, stir and repeat until melted. Wisk in the remaining milk, vegetable oil, vanilla and eggs.
In seperate bowl, add the flour, baking powder,cocoa powder, salt, and sugar and whisk to combine.
Add the chocolate mixture to the dry ingredients and stir until just combined.
Spoon about 1/3 - 1/2 cupfuls of batter into hot waffle iron and cook until done, about 3-5 minutes.
Serve immediately topped with a little powdered sugar and extra chocolate chips, if desired.
Notes
To keep waffles crispy in between cooking, place on wire baking rack to cool.