Preheat the oven to 400ºF.

In a bowl, beat the cream cheese until smooth. Add in the sugar and vanilla and beat to combine.

Unroll the crescent roll dough and separate into 2 long rectangles. Press each into a 12x4-inch rectangle and press the perforations to seal. (If using the crescent recipe creations that comes in one large sheet, unroll the dough and cut lengthwise into 2 rectangles. Press each piece into a 12x4-inch rectangle.)

Spread the cream cheese mixture evenly over the top of the dough. Sprinkle the chocolate chips evenly over the top. 

Starting on the short side, roll up each rectangle and press the edge to seal. With a serrated knife, cut each roll into 5 slices; place the cut side down on an uncreased baking sheet.

Bake for 12-15 minutes, or until golden brown. Remove the cookies from the baking sheet and allow them to cool completely.

In a small bowl, combine the powdered sugar and milk. Drizzle over the cooled cookies.