Preheat oven to 400°F (200°C). Toss cherry tomatoes with 1 tablespoon olive oil, salt, and pepper. Roast on a baking sheet for 15-20 minutes until softened and caramelized.
- Season chicken breasts with salt and pepper. Heat remaining olive oil in a skillet over medium-high heat.
- Cook chicken for 6-7 minutes per side until golden brown and cooked through. Remove from skillet and set aside.
- In the same skillet, add minced garlic and sauté for about 30 seconds until fragrant.
- Stir in basil pesto and heavy cream. Simmer gently until sauce thickens slightly, about 3-5 minutes.
- Return chicken to skillet, spoon creamy pesto sauce over it, and heat through for 2 minutes.
- Add roasted tomatoes to the skillet or serve on the side.
- Sprinkle with Parmesan cheese and garnish with fresh basil if desired.