Place cream cheese in a medium mixing bowl and beat with electric mixer until smooth. Mix in pumpkin, sugar, vanilla, and pumpkin spice until well combined. Gently fold in 2 cups of whipped topping until well incorporated.
Place 12 cookies on work surface. Using 1/3 of filling, spoon on top of cookies. Place another cookie on top of each, then spoon another 1/3 of filling on top of cookies. Repeat with remaining filling and cookies. Gently push down to push filling to edges then place in covered containers.
For best results, keep cakes covered and refrigerate at least 6-8 hours or overnight for cookies to soften.Before serving top with remaining whipped topping and chocolate chips.
SNAPPY TIPS: Be sure the cream cheese is softened to room temperature and beat well to remove lumps before adding other ingredients. Also be sure to refrigerate these cakes for at least 6-8 hours if not longer for the cookies to soften and turn cake like.SNAPPY SUBSTITUTIONS: Instead of pumpkin spice you could use cinnamon, your favorite spice, or omit.