In a medium mixing bowl, use a hand mixer on low speed to combine the milk and sugar until the sugar is dissolved, approximately 1-2 minutes.
Stir in the heavy cream and vanilla.
Slice open your vanilla bean, scrape out seeds and add to the mixture.
Turn the machine on; pour the mixture into freezer bowl, and let mix until thickened, about 20 to 25 minutes. The ice cream will have a soft, creamy texture.
Scoop your ice cream out and into a freezer safe container.
Mix in your crushed chocolate chip cookies and chocolate chips.
If a firmer consistency is desired, transfer the ice cream to an airtight container and place in freezer for about 2 hours. Remove from freezer about 15 minutes before serving.
Enjoy in bowls or on top of cones.