Preheat oven to 400°F (200°C).
Toss cherry tomatoes with 1 tablespoon olive oil, salt, and pepper.
Spread tomatoes on a baking sheet and roast for 20 minutes.
Season chicken breasts with salt, pepper, and Italian seasoning.
Heat remaining olive oil in a skillet over medium heat.
Cook chicken until golden and fully cooked through.
Remove chicken from skillet and set aside.
Add garlic to the skillet and sauté briefly.
Stir in heavy cream and pesto sauce.
Simmer sauce for 3–4 minutes until slightly thickened.
Return chicken to skillet and coat with sauce.
Add roasted tomatoes and gently mix.
Sprinkle with Parmesan cheese and remove from heat.
Garnish with fresh basil and serve warm.