In a medium bowl, with a hand mixer mix together the pudding mix, chilled evaporated milk, and sweetened condensed milk until smooth. Set aside.
In another bowl with a hand mixer, beat cream cheese until smooth.
Add powdered sugar and vanilla extract. Beat again until smooth.
With the mixer running on medium speed, slowly pour in heavy whipping cream. Once the mixture begins to thicken, whip on high speed until stiff peaks form.
Gently fold the whipped cream cheese mixture into the pudding mixture until combined.
For the fresh whipped cream, combine heavy whipping cream powered sugar, and vanilla extract in a tall bowl. Whip with a hand mixer until stiff peaks form, about 2-3 minutes.
Create 2-3 sets of layers in a trifle dish with the pudding cream cheese mixture, fresh whipped cream, banana slices, salted caramel and Salted Caramel Chessmen cookies. End with some of the fresh whipped cream on the top as well as crushed or whole cookies, salted caramel, and fresh mint (if desired).
Refrigerate at least 4 hours before serving.