Preheat oven to 375ºF. Butter a 13x9x2-inch baking dish. Heat olive oil in a heavy large skillet over high heat. Season chicken with salt and pepper and add the chicken to the skillet; sauté until the outside of the chicken is white, about 1 minute per side; transfer to plate. Add the onion and garlic to skillet and sauté until onion begins to soften, about 4 minutes. Add tomato sauce, stewed tomatoes with their juices, wine, pesto and Kalamata olives, and cook until sauce thickens, breaking up tomatoes with spoon, about 8 minutes.
Line buttered baking dish with penne pasta. Arrange chicken over the pasta, and spoon the tomato sauce over it, covering chicken and pasta completely. Mix Vella cheeses in a small bowl, and sprinkle the cheeses over the sauce. Bake until the chicken is just cooked through and sauce bubbles, about 20 minutes.