Heat oven to 350° and spray two 9x5-inch bread pans with nonstick cooking spray.
In a large mixing bowl add the softened butter, sugar, vanilla, and eggs. Beat together until combined.
Add the pumpkin puree and mashed banana. Blend until combined. Batter may look lumpy but that's ok.
In a separate mixing bowl, add the flour, baking powder, baking soda, salt and pumpkin pie spice. Stir with a whisk to break up any clumps.
Add half of the flour mixture into the wet pumpkin mixture and combine together at low speed just until incorporated. Add the other half of the flour and blend in at low speed just until combined.
Stir the 1 tablespoon of flour into the chocolate chips. Add into the pumpkin bread batter and stir together with a wooden spoon or spatula. ** The flour helps the chocolate chips not sink to the bottom of the bread. Reserve some of the chocolate chips (about 1/4 cup) before adding the flour to sprinkle on top of the bread. Or you can just use additional chocolate chips to sprinkle on top.
Divide the batter between the two pans. Loaf pans should be about 1/2 to 2/3 full. Sprinkle the reserved chocolate chips on top of the bread before baking.
Bake for 50-60 minutes. With about 20 minutes left of the cook time, loosely lay a piece of tin foil over the bread to prevent burning. Use a toothpick inserted into the middle to test for doneness. It should come out with only crumbs on it or nothing at all. If it comes out wet, then the bread needs to bake longer.
Let cool in the bread pan for about 15 minutes. Take the bread out and let it cook completely on a cooling rack at room temperature.