Season the chicken with salt and pepper. Add the flour to a shallow bowl. Dredge the chicken through the flour and toss to coat.
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Set large ovenproof (Le Cruset braiseer) skillet with oil over medium-high heat. Add the chicken and sear on both sides until golden, 3-5 minutes per side. Sprinkle the chicken with 1 teaspoon Italian seasoning. Remove the chicken from the skillet to a plate.
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To the same skillet, add the butter, 1 teaspoon Italian seasoning, garlic, orzo, and season with chili flakes. Cook until lightly golden, 2 minutes. Add the broth. Bring to a boil, cook for 3-5 minutes, then add the cream, and pesto. Slide the chicken and any juices left on the plate back into the skillet. Sprinkle over the parmesan. Transfer to the oven and cook, uncovered, for 10 minutes, until the sauce is bubbling around the chicken.
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