Preheat the oven to 400°F (200°C).
Pat chicken breasts dry and season both sides with the Italian seasoning, 1/2 teaspoon salt, and 1/2 teaspoon black pepper.
Heat 1 tablespoon olive oil in an ovenproof skillet over high heat until shimmering. Sear the chicken 1–2 minutes per side until golden brown.
Arrange the grape tomatoes, pressed garlic, and feta around and on top of the chicken in the skillet; drizzle with the remaining 1 tablespoon olive oil.
Transfer the skillet to the preheated oven and bake 15–20 minutes, or until the chicken reaches 165°F (74°C) internal temperature and tomatoes are softened.
Remove the skillet from the oven. Take the chicken out briefly, then mash the feta and tomatoes together in the pan to form a sauce. Stir in the heavy cream and crushed red pepper (if using). Taste and add additional salt and pepper if needed.
Return the chicken to the pan and spoon the sauce over each piece. Serve hot.