Preheat the oven to 375º F.
In a large mixing bowl, whisk together the milk, condensed milk, vanilla, sugar and the beaten eggs and mix well.
Place a medium sauce pan over medium heat and add the butter, apples and cinnamon. Stir and cook for about 7 minutes.
Add bread to milk mixture. Let it stand for about 20 minutes or until bread absorbs most of the mixture.
Add the apples and chocolate chips to the mixture and stir well.
Carefully pour an equal amount of the pudding mixture into the ramekins in the roasting pan. Then add hot water to the roasting pan, not to the ramekins, until the water comes half way up the sides of the ramekins.
Place the roasting pan in the oven and bake for 45 minutes. Serve warm.