Combine all of the ingredients in your blender, except for the chocolate chips and extra cherries. Blend until smooth, adding the extra milk a tablespoon or two at a time as needed, until you get a nice, thick, smooth mixture.
Top with the chocolate chips and extra cherries, and serve.
If your chocolate smoothie bowl base ends up too thin, add more ice cubes until it reaches your desired thickness. You can also add more frozen cherries, if you prefer, but I'm trying to keep your grocery budget in mind here. You can add more by the tablespoon, as needed, to get things moving in your blender. Why might you need extra vegan milk? A bigger banana, your blender, how fresh your chia seeds are, and how hard frozen the cherries are can all make your smoothie thinner or thicker.