Combine diced ripe tomatoes, minced garlic, chopped fresh basil, a drizzle of olive oil, and a splash of balsamic vinegar in a mixing bowl. Season with salt and pepper to taste. Let sit for 15 minutes at room temperature.

Season chicken breasts with salt and pepper, then heat olive oil in a skillet over medium heat. Cook chicken for 3-4 minutes on each side until golden and cooked through. Transfer to a plate to rest.

Boil water in a large pot, season with salt, and cook penne pasta until al dente, about 8-9 minutes. Reserve ¼ cup pasta water before draining.

In the skillet, add more olive oil if needed and the bruschetta mixture. Warm for 1-2 minutes. Add pasta and reserved water, tossing gently to combine.

Slice rested chicken and arrange on top of pasta. Garnish with grated Parmesan and torn basil. Serve immediately or cool for later.