Preheat oven to 350°F. Spray a 9″ x 5″ loaf pan with cooking spray and line the bottom of pan with wax/parchment paper (this makes it easier to remove later on). Sift together flour, cinnamon, baking soda, salt, ginger, nutmeg, cloves, and baking powder in a mixing bowl; set aside.
In a large mixing bowl and using a hand mixer, beat the butter until creamy. Add the brown sugar and beat for a few minutes. Add the eggs one at a time, mixing well after each one. Beat in the pumpkin puree using your mixer.
In a small bowl, stir the vanilla into the pumpkin spice milk. Mix the dry ingredients into the pumpkin mixture in 3 additions on low speed, alternating with the pumpkin milk mixture. Mix until just incorporated. Fold in the chocolate chips.
Spread the batter into an even layer in your prepared pan. Bake for about 1 hour or until a toothpick inserted in the center comes out clean.
Let the loaf cool in the pan for 10 minutes, then turn out onto a rack to cool the rest of the way. Glaze: Mix together the Bourbon and milk; slowly add the powdered sugar to it. Whisk to get the clumps out and then let it sit for 10 minutes to thicken. Add extra powdered sugar, if needed, to thicken.
Pour your glaze over the bread just before serving. Enjoy!