Add the coffee, milk, chocolate chips, sweetened condensed milk, chocolate syrup and vanilla to a blender. Top off the blender with ice and blend until smooth and icy, with tiny chocolate bits throughout. (Add some half-and-half if you'd like it to be a little richer and creamier.)
Serve in glasses with whipped cream on top, and drizzle the whipped cream with chocolate syrup or dot with more chocolate chips.
In a large container, mix the ground coffee with 32 cups (8 quarts) cold water. Cover and allow to sit at room temperature 8 hours or overnight.
Line a fine-mesh strainer with cheesecloth and set over a pitcher or other container. Pour the coffee/water mixture through the strainer, allowing all the liquid to run through. Discard the grounds. Place the coffee liquid in the fridge to chill. Use as needed.