Preheat the oven to 350 degrees F. Spray a 9-by-5-inch loaf pan with nonstick cooking spray; dust with flour and tap out the excess.
Combine the 2 cups flour, 1/4 cup espresso powder, the baking soda, baking powder, cinnamon and salt in a large bowl. Whisk together the granulated sugar, oil, bananas, eggs and vanilla in another large bowl until smooth. Fold in the flour mixture, a third at a time, until just combined after each addition. Fold in 3/4 cup of the chocolate chips. Pour the batter into the prepared pan.
Bake until the bread starts to puff and is just set at the edges, about 40 minutes. Reduce the oven temperature to 325 degrees F, then continue to bake until a toothpick inserted into the center comes out clean, about 35 minutes more. Transfer the pan to a wire rack to cool completely, about 3 hours. Flip the bread out of the pan and place onto a serving platter.
Just before serving, mix the confectioners’ sugar with the remaining 2 tablespoons espresso powder and 1 tablespoon water in a small bowl until smooth. Spread the glaze on top of the banana bread and sprinkle with the remaining 1/4 cup chocolate chips.