Heat oven to 375°F. Cook bacon in a skillet until crisp; transfer to a bowl, leaving 1 tablespoon fat.
Cook onion in fat 5 minutes. Add sauerkraut and caraway; cook 3 minutes. Mix with bacon; cool slightly.
Cut a deep pocket in each chop without cutting through. Divide filling among pockets; secure with toothpicks. Season outsides with salt and pepper.
Heat oil in an ovenproof skillet. Brown chops 2 minutes per side. Transfer to oven; bake 20–30 minutes until the center of the stuffing reaches 165°F.
Rest 3 minutes; remove toothpicks before serving.