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Preheat oven to 425°F with rack in center position. Pat the chicken dry, then transfer to a rimmed baking sheet. Cut the butternut squash into 2-inch cubes, if needed. Core and slice the apples into thin wedges.
To baking sheet, add butternut squash and apples. In a small bowl, combine the oil, honey, rosemary, and cinnamon. Season with salt and pepper. Drizzle half of oil mixture over butternut squash and apples, tossing to combine. Season with salt and pepper, then brush remaining glaze on chicken.
Bake 30–35 min., until squash is tender and internal temperature of chicken reaches 165°F and juices run clear.