Begin by preheating your oven to 375°F (190°C) to ensure it reaches the perfect temperature for cooking your chicken.
Prepare the chicken breasts: Place them on a cutting board and carefully slice horizontally into the side of each breast to create a pocket. Make sure not to cut all the way through; the base should remain intact to hold the filling.
In a medium-sized mixing bowl, combine the halved cherry tomatoes, halved mozzarella balls, chopped fresh basil, balsamic glaze, minced garlic, salt, and pepper. Gently fold the ingredients together until well mixed, creating a vibrant and flavorful filling.
Generously spoon the tomato and mozzarella mixture into each chicken breast pocket, ensuring each one is well filled to optimize the flavors.
To secure the stuffing, gently close the openings of the chicken breasts and use toothpicks or kitchen twine to hold them shut, preventing any of the delicious filling from spilling out during cooking.
In a large, oven-safe skillet, heat the extra virgin olive oil over medium-high heat. Once hot, add the stuffed chicken breasts, searing them for about 3-4 minutes on each side, or until they develop a beautiful golden-brown crust.
Once browned, sprinkle the Italian seasoning over the chicken breasts for an added depth of flavor. Carefully transfer the skillet to your preheated oven and bake for approximately 20-25 minutes, or until the chicken is cooked through and reaches an internal temperature of 165°F (74°C).
After baking, remove the skillet from the oven and let the chicken rest for 5 minutes. Then, remove the toothpicks or twine with care to avoid any injury.
For serving, drizzle any remaining juices from the skillet over the sliced chicken. Garnish with additional fresh basil leaves for a pop of color and flavor, if desired.