Preheat oven to 350 degrees.
Cut the bread into 1-inch pieces. Spread bread pieces on a cookie sheet. Place in preheated oven and toast bread pieces for 10 minutes. Remove from oven and allow to cool.
Spoon cherry pie filling into bottom of a buttered 13 x 9-inch pan.
In a large mixing bowl using an electric mixer on medium speed, combine butter, sugar, cinnamon and vanilla extract; blend well.
Blend in eggs. Add the milk and blend well.
Add toasted bread pieces to egg mixture along with the chocolate chips. Stir to blend. Allow to soak for 10 minutes. Spoon bread mixture over pie filling in pan.
Cover with foil and bake for 35 minutes. Remove foil and bake for an additional 10 minutes or until the top is lightly browned and the custard is set but still moist.
Spoon into serving bowls with cherries on the top. Serve warm with large squirts of whipped cream.