Pat the chicken breasts dry and season both sides with the salt, Italian seasoning, onion powder, garlic powder, and black pepper.
1½ to 2 pounds boneless skinless chicken breasts, 2 teaspoons kosher salt, 1 teaspoon Italian seasoning, 1 teaspoon onion powder, 1 teaspoon garlic powder, ½ teaspoon black pepper
Heat the olive oil in a large skillet over medium. Sear the chicken, flipping every few minutes, until deeply golden on both sides, 6 to 8 minutes per side. The chicken will not be cooked through. Transfer to a plate.
2 tablespoons olive oil
Add the remaining olive oil and the shallot to the skillet and cook until softened, about 3 minutes. Stir in the garlic and red pepper flakes and cook until fragrant, about 1 minute.
2 tablespoons olive oil, 1 large shallot, 8 cloves garlic, ¼ to ½ teaspoon red pepper flakes
Add the cherry tomatoes whole, along with the salt and black pepper. Cook over medium-high, stirring only occasionally, until the skins blister and split, 8 to 10 minutes.
1½ pounds cherry tomatoes, ½ to 1 teaspoon kosher salt, ¼ to ½ teaspoon black pepper
Pour in the wine and add the oregano sprigs, if using. Simmer, scraping up the browned bits, until reduced and glossy, 4 to 5 minutes.
¾ cup dry white wine, 3 to 4 sprigs fresh oregano
Remove the oregano sprigs. Smash about half the tomatoes against the pan. Stir in the basil, then nestle the chicken back in with any juices. Cover and cook until the chicken registers 165°F at the thickest part, 5 to 8 minutes.
Handful of fresh basil