Heat oven to 350°F. Spray 12x8-inch (2-quart) glass baking dish with cooking spray. Place bread and cranberries in baking dish; toss to mix.
In large bowl, with wire whisk, beat eggs, brown sugar, cocoa and half-and-half until well blended. Pour over bread mixture. Stir mixture gently with large spoon to coat bread with liquid. Let stand 10 minutes. Stir mixture.
Bake uncovered 45 to 50 minutes or until knife inserted in center comes out clean.
In 1-quart saucepan, mix granulated sugar, butter, baking chips and whipping cream. Cook over medium heat 3 to 4 minutes, stirring frequently, until slightly thickened and smooth. Remove from heat; stir in bourbon (sauce will be thin). Serve sauce over warm bread pudding.