Combine whole milk, half and half, vanilla instant pudding mix, and cherry whiskey in a large bowl. Mix until smooth and well combined.
Pour the prepared Cherry Garcia Ice Cream mixture into the Ninja Creami pint container and place it on a level surface. Allow it to freeze for at least 24 hours until firm.
Place the frozen Ninja Creami pint container into the Ninja Creami Machine, and process, using the "Ice Cream Setting."
Remove the pint container from the Ninja Creami machine and use a spoon to clear a hole down to the bottom of the ice cream in the container. Place the cherries into the hole.
Place the pint container back into the Ninja Creami Machine and process using the "Mix-In Setting."
Remove the pint container from the Ninja Creami machine and use a spoon to clear a hole down to the bottom of the ice cream in the container. Place the chocolate chips into the hole.
Place the pint container back into the Ninja Creami Machine and process using the "Mix-In Setting."