In a greased 9×13 casserole dish, place a single even layer of Chessman cookies on the bottom.
Top the cookies with a layer of sliced bananas.
In a bowl, whisk together the milk and instant pudding mix until thick and creamy.
In a separate bowl, beat together the cream cheese and condensed milk until smooth.
Fold the whipped topping into the cream cheese mixture.
Add the pudding mixture to the cream cheese and whipped topping mixture, and stir until completely combined.
Pour the mixture over the bananas and cookies in the casserole dish, and smooth into an even layer.
Top the pudding with another layer of Chessman cookies. Refrigerate to chill before serving.
Enjoy!