Mix 1/4 cup olive oil, garlic, onion powder, pepper, and salt together in a bowl. Place chicken breasts into a shallow dish and pour marinade over top. Refrigerate for at least 4 hours.
Meanwhile, heat balsamic vinegar in a small saucepan to a slow boil. Allow to boil for 15 minutes, watching carefully to prevent burning. Cook until vinegar has reduced to half the original volume. Remove from the stove and let cool completely.
Preheat the oven to 400 degrees F (200 degrees C). Remove chicken from marinade and shake off excess. Discard remaining marinade.
Layer the basil, mozzarella cheese, and tomato slices evenly onto each piece of chicken. Roll chicken up and secure with toothpicks.
Heat olive oil in an oven-safe skillet over medium heat. Add stuffed chicken breasts and sear until browned, 3 to 4 minutes per side.
Transfer the skillet to the preheated oven and bake until chicken is no longer pink in the center and the juices run clear, about 10 minutes. An instant-read thermometer inserted into the center should read at least 165 degrees F (74 degrees C).
Allow stuffed chicken breasts to rest for 5 minutes. Drizzle with balsamic reduction before serving.
Nutritional Facts
Per 4 servings
Calories: 489
Carbohydrate: 9g
Fat: 33g
Fiber: 1g
Protein: 39g
Sugar: 6g
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