Heat your oven to 350°F and grease a loaf pan really well with butter or cooking spray. I always line mine with parchment paper too because it makes cleanup so much easier. This step takes literally two minutes but saves you from frustration later.
Mash your 3 ripe bananas in a large bowl until they're pretty much smooth — a few small lumps are totally fine. Pour in the melted butter, then crack in your 2 eggs and add the vanilla extract. Stir everything together until it's combined and you've got that gorgeous golden-brown mixture.
In a separate bowl, whisk together your 1 1/2 cups flour, 3/4 cup granulated sugar, 1/4 cup brown sugar, 1 tsp baking powder, 1/4 tsp baking soda, and 1/4 tsp salt. This takes maybe a minute and keeps lumps from hiding in your batter.
Pour the dry ingredients into your banana mixture and stir until just combined — don't overmix or your bread gets dense. Add your 1/4 cup milk and fold it in gently until the batter comes together. Some streaks of flour are actually okay here.
Fold in your 1/2 cup chocolate chips carefully so they're spread throughout the batter. I always save a handful to sprinkle on top because it makes the loaf look prettier when it comes out of the oven. This step's where the magic happens for chocolate chip banana bread texture.
Pour everything into your prepared loaf pan and smooth the top with a spatula. Sprinkle those reserved chocolate chips on top if you want that bakery-style look. Bake at 350°F for 50 to 55 minutes — mine usually needs the full 55, but ovens vary a little.
The bread's done when a toothpick inserted in the center comes out with just a few moist crumbs attached, not wet batter. Let it cool in the pan for about 10 minutes, then turn it out onto a wire rack. Don't slice it until it's completely cool or it'll fall apart, trust me on this one.