Bring a large pot of salted water to a boil. Add the penne and cook according to the package instructions until al dente. Drain and set aside.
Season the chicken breast filets with some of the dried Italian herbs, salt and black pepper on both sides.
In a large skillet, heat half the olive oil over medium-high heat. Add the chicken breasts and cook for about 5 minutes on each side, or until fully cooked and no longer pink in the center. Remove the chicken from the skillet and set aside.
In the same skillet, over medium heat, add the remaining olive oil. Add the minced garlic and sauté for just 30 seconds until fragrant. Watch carefully as it can burn easily.
Pour in the heavy cream and bring to a gentle simmer. Let it cook for 2-3 minutes to thicken slightly.
Reduce the heat to low and gradually stir in the grated Parmesan cheese until it’s melted and the sauce is smooth.
Add the remaining Italian herbs and stir to combine. Taste and adjust the seasoning as needed.
Slice the cooked chicken into thin strips. Add the chicken slices and halved cherry tomatoes to the sauce. Toss to combine and cook until warmed up, about 3 minutes.
Add the cooked pasta to the skillet and gently toss to coat the pasta with the creamy sauce, chicken, and tomatoes.
Divide the Chicken Garlic Parmesan Pasta among serving plates. Garnish with fresh basil leaves and red pepper flakes if desired.