Preheat oven to 375 degrees. Season pork with salt and pepper. Heat a large ovenproof skillet over medium-high heat; swirl in oil. Cook chops until golden brown, turning once, about 8 minutes. Transfer to a plate. Remove all but 2 tablespoons fat from skillet.
Reduce heat to medium. Add potatoes and onion; season with salt. Cook until golden in spots, about 10 minutes. Add vinegar and cider. Cover and simmer, stirring a few times, until potatoes are tender, about 5 minutes. Sprinkle with caraway seeds. Return pork and juices to skillet; tuck apple slices between chops. Roast until a thermometer inserted into thickest part of chops (without touching bone) registers 138 degrees, about 10 minutes. Serve pork, vegetables, and apples with pan juices.