In a mixing bowl, combine diced Roma tomatoes, minced garlic, chopped fresh basil, olive oil, and balsamic vinegar. Season generously with salt and pepper and stir well to coat the tomatoes. Let this vibrant Bruschetta topping marinate for at least 15 minutes at room temperature.

While the bruschetta toppings marinate, slice boneless, skinless chicken breasts into cutlets. Heat olive oil in a skillet over medium-high heat. Add the seasoned chicken cutlets, cooking for about 5-7 minutes on each side until golden brown and cooked through. Once cooked, let them rest before slicing into strips.

Fill a large pot with salted water and bring it to a boil. Add penne pasta and cook according to package instructions, typically around 8-9 minutes for al dente. Save ¼ cup of the starchy pasta water before draining.

In the same skillet used for chicken, add the reserved pasta water and the marinated bruschetta topping. Heat gently over low heat for about 2-3 minutes while stirring.

Add the drained pasta and sliced chicken to the skillet, tossing everything together until well combined and heated through, about 2-3 minutes. Serve immediately, garnished with grated Parmesan cheese and fresh basil leaves.