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Preheat the oven to 425 degrees F. Sprinkle the chicken generously with salt and pepper. Heat 2 tablespoons of the olive oil in a large, deep ovenproof skillet over medium-high heat. Place the chicken in the skillet skin-side down and cook, flipping once, until golden on both sides. Transfer to a plate.
Reduce the heat to medium, add the thyme and leeks to the skillet and cook, stirring occasionally, until softened, about 4 minutes. Pour in the balsamic and wine and use a wooden spoon to scrape up any browned bits from the bottom. Cook until the skillet is nearly dry. Stir in the broth, apple cider and a pinch of salt and pepper and bring to a boil.
Use a fork to mash the flour with the remaining olive oil together in a small bowl until smooth. Whisk the butter-flour mixture into the skillet until dissolved. Stir in the apples and remove from the heat. Nestle the chicken skin-side up in the skillet along with any collected juices from the plate. Bake until the chicken is cooked through, about 25 minutes.
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