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Prepare Chicken: Season chicken evenly with ¾ tsp. salt and ¼ tsp. black pepper. Brush ¼ cup of the pesto evenly over both sides. Let sit for 15 minutes.
Cook Chicken: Heat 2 Tbsp. olive oil in a large skillet over medium. Once hot, arrange chicken in pan and cook, undisturbed, for 5 minutes, until golden. Flip, and cook 2 more minutes; transfer chicken to a clean plate.
Cook Orzo Mixture: Add onion to pan and cook until softened, about 3 minutes. Stir in red pepper flakes and orzo; cook 1 to 2 minutes to lightly toast grains. Add broth, remaining ¼ cup pesto, ½ tsp. salt, and ¼ tsp. black pepper. Bring mixture to a boil and nestle chicken back into pan. Sprinkle Parmigiano-Reggiano cheese overtop and reduce heat to medium-low. Cover, and gently simmer for about 15 minutes, until the orzo is al dente. If the liquid is not mostly absorbed by this point, remove lid and continue cooking, uncovered, for 1 to 3 more minutes.
Prepare Tomato-Basil Topping: Combine tomatoes, basil, garlic, and remaining 2 Tbsp. olive oil in a medium bowl. Season with a good pinch of salt.
Garnish: Spoon tomato-basil mixture over chicken and orzo. Garnish with extra Parmigiano-Reggiano cheese, if desired, and serve.