In a medium bowl, combine the halved cherry tomatoes, finely diced red onion, minced garlic, and chopped fresh basil. Pour in 2 tablespoons of extra virgin olive oil and 1 tablespoon of balsamic vinegar. Season with a pinch of salt and black pepper. Toss thoroughly and set aside at room temperature so the flavors marry.

Bring a large pot of salted water to a rolling boil. Add the penne pasta and cook according to package directions until al dente. Drain completely (do not rinse) and set aside.

Pat the chicken breasts dry and season both sides evenly with Italian seasoning, garlic powder, salt, and black pepper. Heat 1 tablespoon of olive oil in a large skillet or grill pan over medium-high heat. Cook the chicken for 5 to 7 minutes per side, until golden brown and cooked through (internal temp 165°F). Remove to a cutting board, let rest for 5 minutes, then slice into thin strips.

Lower the skillet heat to medium. Pour the marinated tomato mixture directly into the warm skillet. Stir and cook for just 1 to 2 minutes until the garlic is fragrant and the tomatoes are gently warmed through.

Add the cooked penne pasta directly into the skillet with the warmed tomatoes. Toss everything well for 30 seconds so the pasta absorbs the seasoned juices.

Transfer the pasta and tomatoes to a large serving bowl. Arrange the sliced grilled chicken strips neatly on top. Finish the dish by sprinkling grated Parmesan cheese and extra fresh basil leaves over the top. Add an optional extra drizzle of balsamic glaze if desired.