In a small saucepan over medium heat add chocolate chips, milk, cocoa powder, sugar and vanilla. Continue to stir until chocolate is fully melted.
Add melted chocolate mixture into a blender, along with avocado and bananas and blend, until it's thick and creamy. This will take about 2 minutes to achieve creaminess consistency, careful not to overblend.
Pour the mixture into popsicle molds and freeze for at least 4 hours, or until firm. I recommend freezing overnight to make sure they're firm.