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Preheat the oven to 350 F, and position a rack in the center of the oven. Line two standard-sized loaf pans with a sheet of parchment paper to easily remove the bread after it bakes.
In a large bowl, whisk together the pumpkin, sugars, oil, eggs, milk and vanilla until smooth. In a separate bowl, sift together the flour, baking soda, salt and spices.
Add the dry ingredients to the wet and use a spatula to combine the batter just until moistened. Fold in the chocolate chips, reserving ¼ cup to sprinkle on top of the batter.
Divide the batter between the pans. Sprinkle the rest of the chocolate chips over the batter, using a few extra if you like more on top. I like to also sprinkle a few mini sized chocolate chips on top, since the different sizes look really pretty.
Bake the bread on the center oven rack for about 55-65 minutes, until a cake tester or toothpick inserted in the center comes out clean, or with moist crumbs clinging to it.
Cool the bread in the pans for 15 minutes, then lift the bread out of the pans by grasping the ends of the parchment paper sling. Let the bread cool on a cooling rack for several hours before cutting and serving.