Beat the butter and the sugar together until light and fluffy, 2 mins. Beat in the salt and then alternate adding the flour and the milk until just combined.
Stir in the vanilla extract and chocolate chips. Line a sheet tray with wax or parchment paper. Drop teaspoons of the cookie dough onto the prepared sheet.
Ice Cream: Stir the sweetened condensed milk and the vanilla together in a large bowl.
In a separate large bowl, whip the heavy cream until you have stiff peaks.