In a medium saucepan, combine the chopped cherries and 1/2 cup of sugar over medium heat. Stir occasionally until the cherries start to break down and release their juices (about 5-7 minutes).
Remove the saucepan from heat and stir in the lemon juice and vanilla extract. Allow the cherry mixture to cool to room temperature.
In a mixing bowl, whisk together the heavy cream, whole milk, and the remaining 1/2 cup of sugar until the sugar is dissolved and the mixture is well combined.
Once the cherry mixture has cooled, fold it into the cream mixture. Stir to combine thoroughly.
Pour the mixture into an ice cream maker and churn according to the manufacturer's instructions until it reaches a soft-serve consistency (usually about 20-25 minutes).
During the last few minutes of churning, slowly add the chocolate chips to the mixture.
Transfer the churned ice cream to an airtight container and freeze for at least 4 hours, or until firm.
Notes
Serve in chilled bowls topped with additional chocolate chips and a sprig of mint for a fresh touch. Enjoy!