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One at a time, put each chicken breast between 2 pieces of plastic wrap and pound with the flat side of a meat mallet or a heavy skillet until uniform in thickness (about ½ inch thick). Put the chicken in a baking dish or shallow bowl.
For the pesto: Pulse the basil, parmesan, pine nuts, lemon juice, garlic, ½ teaspoon salt, and ¼ teaspoon pepper in a food processor until combined. With the food processor running, drizzle in ⅓ cup olive oil and process until the pesto is smooth.
Pour ⅔ cup of the pesto over the chicken and toss to coat. Refrigerate the remaining pesto.
Toss the tomatoes with the remaining 1 tablespoon olive oil, ½ teaspoon salt, and a pinch of pepper in a medium bowl. Oil a grill or grill pan and heat over medium heat. Grill the chicken until well marked and a thermometer inserted into the center registers 165˚F, about 5 minutes per side. Transfer to a cutting board to rest. Grill the tomatoes until hot and well marked, about 2 minutes per side.
Drizzle the chicken with the remaining pesto and serve with the grilled tomatoes, salad, and crusty bread.