Prepare the cherries by washing, pitting, and halving them.
In a mixing bowl, whisk together the heavy cream, whole milk, and granulated sugar until smooth.
Add in the vanilla extract and whisk until fully incorporated.
Stir in the halved cherries and semi-sweet chocolate chips gently.
Cover the mixture and chill in the refrigerator for at least 2 hours.
Pour the chilled mixture into an ice cream maker and churn according to the manufacturer's instructions.
Once the ice cream is at a soft-serve consistency, transfer it to an airtight container.
Freeze the ice cream for at least 4 hours until firm.