In a medium mixing bowl, combine diced Roma tomatoes, minced garlic, fresh basil leaves, olive oil, balsamic vinegar, salt, and pepper. Stir gently to combine and let the mixture sit at room temperature for 15 minutes.

Slice the chicken breasts into cutlets. Season with oregano, garlic powder, salt, and pepper. Heat a skillet over medium-high heat with olive oil, add chicken, and cook until golden brown, about 3-4 minutes per side.

Fill a pot with water, add salt, and bring it to a boil. Add penne pasta and cook until al dente, approximately 8-9 minutes. Reserve 1/4 cup of pasta water, then drain the pasta.

In the same skillet, reduce heat and add the bruschetta mixture. Warm for 1-2 minutes. Add warm pasta and toss gently, then layer in the sliced chicken.

Transfer the pasta to serving plates and garnish with freshly grated Parmesan cheese and torn basil leaves. Serve immediately.