Preheat waffle maker. In a small saucepan, cook and stir sugar and 1/2 cup water over medium heat until sugar is dissolved. Add cherries; cook and stir until cherries are tender, 3-5 minutes. Mix cornstarch and remaining 2 tablespoons water until smooth; stir into pan. Bring to a boil; cook and stir until thickened, 1-2 minutes. Remove and keep warm.
In a large bowl, whisk flour, baking powder, cinnamon and baking soda. In another bowl, whisk buttermilk, eggs, oil and extract until blended. Add to dry ingredients; stir just until moistened. Stir in cherries and chocolate chips. Bake waffles according to manufacturer’s directions until golden brown. Serve with cherry syrup, and additional chocolate chips if desired.
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