Combine chocolate chips, milk, cocoa powder, sugar, cinnamon, and vanilla extract in a saucepan over low heat; stir until all ingredients are melted and combined, about 5 minutes.
Place avocado and banana in blender; blend until smooth. Add chocolate mixture into the puree; blend until the mixture is the consistency of pudding, about 5 minutes. Pour the pudding into ice pop molds, and place into freezer until firm, about 3 hours.
