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.
Recipe courtesy of Ree Drummond