Roast the Tomatoes
Preheat oven to 400°F (200°C). Place grape tomatoes on a rimmed baking sheet and toss with 2 tablespoons olive oil, salt, and black pepper. Spread the tomatoes evenly across the sheet and roast for 20 minutes until they're blistered and beginning to burst, releasing their sweet juices.
Season and Prepare the Chicken
Pat the chicken breasts dry with paper towels to ensure proper browning. Season all sides generously with garlic powder, paprika, salt, and black pepper, pressing the seasonings into the meat to adhere well.
Cook the Chicken
Heat 2 tablespoons olive oil in a large skillet over medium heat until shimmering. Add the seasoned chicken breasts and sear until golden brown and cooked through, approximately 5 minutes per side or until internal temperature reaches 165°F (74°C). Transfer the chicken to a plate and tent with foil to keep warm.
Prepare the Sauce Base
In the same skillet, cook the chopped onion in the remaining oil and chicken drippings until soft and slightly caramelized, about 3-4 minutes. Add more oil if needed. Add the minced garlic and cook for just 30 seconds until fragrant, being careful not to burn it.
Create the Cream Sauce
Add the basil pesto to the skillet and stir to combine with the onions and garlic. Pour in the heavy whipping cream and add the grated parmesan cheese, stirring gently to incorporate. Allow the sauce to come to a gentle simmer, which will thicken it slightly and meld the flavors together.
Combine and Serve
Return the seared chicken breasts to the skillet, nestling them into the creamy sauce. Add the roasted tomatoes, spooning some of the sauce over the chicken. Let everything reheat for 2-3 minutes. If desired, sprinkle with red chili pepper flakes for a hint of heat. Serve immediately, garnished with additional parmesan and fresh basil if available.