In a bowl, combine the milk and sugar and whisk until the sugar is dissolved. Add the heavy cream and vanilla extract and stir to combine. Refrigerate for at least one hour.
Pour the mixture into your ice cream maker and follow the manufacturer's instructions. After approximately 20 minutes, after the mixture is thickened, add the crushed chocolate sandwich cookies and let it continue to churn for another 5-10 minutes or until the ice cream is nice and thick. Spoon the ice cream into a freezer safe container with a lid and freeze for at least 2-3 hours until firmly set. Makes about 1 quart.