Place a glass or metal mixing bowl in the freezer to chill. Wash and dry 4 jars.

Combine milk, instant banana pudding, dry whipped topping mix, and vanilla extract in a bowl. Beat using an electric mixer until soft peaks form. Place in the refrigerator.

Reserve 2 sandwich cookies and cut them in half. Reserve 4 dried banana chips. Combine remaining cookies and and remaining banana chips in a food processor and blend until coarsely crumbled.

Combine milk, dry whipped topping mix, and vanilla extract in a bowl; mix using an electric mixer on low speed until blended.

Spoon 2 tablespoons crumble into the bottom of each jar. Add a layer of 4 to 6 banana slices. Add 2 to 3 tablespoons banana pudding mixture. Top with 4 tablespoons whipped cream. Repeat layers until jars are filled. Top each jar with whipped cream, half a cookie, and 1 banana chip standing upright. Refrigerate until ready to serve.