Preheat the oven to 325 degrees F and grease a 9x5-inch loaf pan or line with parchment paper.
Whisk together flour, baking powder, baking soda, cinnamon, and salt in a bowl. Set aside. Beat sugar and butter together in a large bowl with an electric mixer until light and fluffy; add eggs one at a time, beating well after each addition. Mix in bananas, milk, and vanilla. Mix in flour mixture until just blended. Fold in chocolate chips (saving a few for the top) and pour batter into the prepared loaf pan. Sprinkle reserved chocolate chips on top.
Bake in the preheated oven until a toothpick inserted into the center comes out clean, about 60-70 minutes, covering with aluminum foil if getting too brown at the end. Cool in the pan for a little bit before slicing.