Whip the cream using a balloon or electric whisk until the cream holds its form in stiff peaks. Set to one side.
In a blender, combine large pieces of the peeled banana, milk, vanilla ice cream, ground cinnamon, and 2 ½ tablespoons of the salted caramel sauce. Blend the ingredients until everything is combined and the shake reaches a smooth consistency.
Pour the milkshake into two tall milkshake glasses. Top with the whipped cream, chopped pecan nuts, dried banana chips, and the remaining ½ tablespoon caramel sauce. Serve immediately.