Preheat oven to 425°F. Heat oil in large ovenproof skillet over high heat. Sprinkle chicken with salt and pepper. Add chicken to skillet; cook until skin is crisp and browned, about 6 minutes per side. Transfer chicken to plate. Reduce heat to medium-high. Drain all but 2 tablespoons drippings from skillet. Add shallots; stir until soft and beginning to brown, about 2 minutes. Add garlic; stir 30 seconds. Add Sherry; boil until reduced by half, scraping up browned bits, about 3 minutes. Add chicken broth; bring to boil. Return chicken, skin side up, to skillet. Place orange wedges and olives among chicken pieces. Transfer to oven and braise uncovered until chicken is cooked through, about 20 minutes.
Transfer chicken to platter. Bring sauce to boil over high heat. Stir in honey; boil until thickened, about 5 minutes. Season with salt and pepper. Pour sauce, oranges, and olives over chicken, or return chicken to skillet and serve.