For the roasted tomatoes: Preheat the oven to 375 degrees F. Line a rimmed baking sheet with parchment.
Arrange the tomatoes cut-side up on the prepared baking sheet. Sprinkle with the salt and pepper and drizzle with the olive oil. Bake for 15 minutes. Set aside and leave the oven on.
While the tomatoes roast, make the pesto: Combine the sun-dried tomatoes, basil, Parmesan, pine nuts, garlic, red pepper flakes and salt in a food processor. With the machine running, stream in the olive oil and process until the pesto is emulsified.
For the chicken: Spread 1 tablespoon of the pesto over each chicken breast, sprinkle with Parmesan and then top each with 2 slices of the provolone. Wrap 3 slices of the prosciutto around each chicken breast and the toppings.
Place the chicken breasts on the same baking sheet with the roasted tomatoes and bake for another 20 minutes. Set aside.
For the salad: Toss the arugula with the extra-virgin olive oil and lemon juice in a large bowl.
Divide the tomatoes among plates, top each with the chicken and the arugula salad. Enjoy!