In a large bowl combine sugar, flour and cinnamon.
Add apples and vanilla; toss to coat.
Transfer to pastry lined pie pan.
Combine caramel apple dip and milk; drizzle over apples.
For topping, in a mixing bowl combine flour and brown sugar. Cut in butter and sprinkle over apples.
Bake 350 degrees F for 50-55 minutes.
Remove from oven.
To serve, top with additional caramel apple dip and ice cream.