Preheat oven to 350 degrees. Line two 9x5 loaf pans with foil or parchment paper. Spray the foil/parchment paper and pan with nonstick baking spray.
In a large bowl, add the sugar and butter. Beat with a hand mixer until well combined.
Add in the eggs, pumpkin, and vanilla. Beat until the eggs are pumpkin are incorporated.
In a separate bowl, add the flour, baking powder, baking soda, salt, and pumpkin pie spice. Whisk until combined.
Alternate adding the flour and buttermilk to the wet ingredients starting and finishing with the flour. Beat until each addition is incorporated.
Fold in the chocolate chips.
Split the batter between two 9x5 loaf pans, top with a few extra chocolate chips for presentation, and bake for 45-50 minutes. Allow the loaves to cool for 10 minutes and then transfer to a cooling rack.
Store covered at room temperature for several days.