In a 9x13 glass dish spread out the ice cream evenly. Cover and place in freezer. Freeze to set for 2 hours.
While the ice cream is setting start making the cookie topping. Preheat oven to 350 degrees. Cream butter and sugars in a medium bowl. Stir in vanilla and flour until well mixed. Spread dough into a foil-lined 8x8 baking dish. Bake for 15 minutes or slightly golden. Remove from heat and let stand until completely cooled.
Once Ice cream is all set and cookie topping is completley cooled, take ice cream out of freezer. Pour the caramel sauce evenly over ice cream. Break apart the cookie topping into big chunks and sprinkle evenly over caramel.
Melt chocolate chips in a microwavable bowl. Heat at 30 second intervals until melted. Stir and then drizzle over the cookie topping. Re-cover and place back into freezer for 6 hours or overnight to completely re-freeze. Slice into squares and serve.