Preheat the oven to 400°F. Season the chicken with salt and pepper, then lightly coat with flour.
Heat a large oven-safe skillet over medium-high heat. Cook the prosciutto until crisp, then remove and set aside.
In the same skillet, add 3 tablespoons of butter. Add the chicken, shallots, garlic, and thyme. Sear the chicken until golden, about 3–5 minutes per side.
Add 1 tablespoon butter, the sage, orzo, 1 1/2 cups of tomatoes, and season with chili flakes. Cook for 2 minutes, until the orzo is lightly toasted.
Pour in the wine and 2 cups of water or broth. Bring to a boil and cook for 3–5 minutes. Stir in the cream and parmesan. Transfer the skillet to the oven and bake, uncovered, for 10 minutes, until the sauce is bubbling and the chicken is cooked through.
Serve topped with 1/2 cup fresh tomatoes, basil, thyme, and the crispy prosciutto.