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Make the jam: in a medium saucepan over medium heat, combine the cherries and maple syrup. Cook, stirring occasionally and breaking up the cherries with your spoon, for 10-15 minutes, or until the cherries have broken down with a few small pieces remaining. Remove from heat and stir in the chia seeds, then transfer to fridge to firm up for at least 4 hours.
Make the chia pudding: In a medium bowl, whisk together the chia seeds, cocoa powder, maple syrup, vanilla, salt, and milk until cocoa powder is fully dissolved and all ingredients are combined. Cover and transfer to fridge to firm up for at least 4 hours.
Make the parfaits: Divide ⅔ of the chia pudding mixture between four jars or airtight containers. Add ¼ cup Greek yogurt to each jar, then add 1-2 Tablespoons of cherry chia jam, followed by the remaining chia pudding and an additional dollop of yogurt if desired. Serve topped with grated chocolate if you're feeling extra luxurious.