Preheat oven to 350°F. Line a baking sheet with parchment paper or a Silipat (if you just have a cookie sheet, spray very well with cooking spray).
Stir together raspberries, chia seeds, and maple syrup in a medium pot over low heat. Bring to a gentle boil before and simmer, uncovered, for about 10 minutes (stirring frequently) until mixture thickens. Remove from heat and stir in vanilla. Pour into a bowl and place in freezer to cool.
In a small bowl, stir together flax and water to make a “flax egg.” Set aside to set for 5 minutes.
Scoop the dough into one inch balls. Place two inches apart on prepared baking sheet and gently flatten cookies with hands (they won’t spread much while baking.) Use your thumb to make a small indentation in each cookie. Fill each cookies 1/2 tsp chia jam.
Bake for 11 minutes. Allow cookies to cool on the pan for 10 minutes before transferring to a rack to cool completely.