In a medium bowl, combine the cherry tomatoes, mozzarella, fresh basil, minced garlic, olive oil, balsamic glaze, oregano, and a pinch of salt and pepper. Mix well to combine the flavors.
Take the chicken breasts and carefully cut a pocket in each breast by slicing them horizontally, being cautious not to cut all the way through.
Stuff each chicken breast with the Caprese mixture, dividing it evenly between the two. Secure the openings with toothpicks or tie them with kitchen twine to keep the filling inside.
Season the outside of the stuffed chicken breasts with additional salt, pepper, and a drizzle of olive oil for extra flavor.
Place the stuffed chicken breasts in a baking dish. If desired, drizzle a bit more balsamic glaze over the top for added flavor and presentation.
Bake in the preheated oven for 25-30 minutes, or until the chicken is cooked through and reaches an internal temperature of 165°F (74°C).
Remove the chicken from the oven and let it rest for about 5 minutes before slicing.
Serve warm, drizzled with extra balsamic glaze if desired, and sprinkle fresh basil on top for garnish.
Notes
Let the chicken rest before slicing for juicier meat.