Cut the chicken breasts into bite-sized cubes and season with Italian seasoning, kosher salt, and pepper. Heat olive oil in a large non-stick skillet and sauté the chicken over medium-high heat until golden and fully cooked, about 7–8 minutes. Set aside.
While the chicken cooks, bring a pot of salted water to a boil. Add your pasta and cook according to the package instructions until al dente. Reserve a cup of the pasta water before draining.
Lower the skillet’s heat and stir the heavy cream, Parmesan, and sun-dried tomatoes into the pan with the cooked chicken. Stir until the sauce combines and has a creamy consistency. If the sauce is too thick, add reserved pasta water, a few tablespoons at a time.
Add the cooked, drained pasta to the skillet and toss to coat everything in the sauce. Turn off the heat, mix in the pesto, and taste for seasoning. Sprinkle red pepper flakes for a subtle kick.
Top the pasta with basil leaves and extra grated Parmesan. Serve hot and enjoy!