Preheat your oven to 400°F (200°C).
Place the cherry tomatoes on a baking sheet, drizzle with half of the olive oil and a pinch of sea salt, then roast for 15 minutes until they begin to burst.
Bring a large pot of salted water to a boil and cook the whole grain penne according to the package directions until al dente.
While the pasta is boiling, heat the remaining olive oil in a large skillet over medium-high heat.
Dice the chicken breast into bite-sized pieces and season with the remaining sea salt and black pepper.
Sauté the chicken in the skillet until golden brown and cooked through, approximately 6 to 8 minutes.
Add the minced garlic and red pepper flakes to the skillet with the chicken and cook for 1 minute until highly fragrant.
Drain the cooked penne, reserving about 0.25 cup of the starchy pasta water.
Add the cooked penne, roasted tomatoes (including any juices from the pan), and the reserved pasta water to the skillet.
Toss everything together over low heat for 1 to 2 minutes until the sauce coats the pasta evenly.
Remove from the heat and stir in the fresh chopped basil and parmesan cheese before serving immediately.