Cut off excess skin from each drummette; discard. Place drummettes in large resealable food-storage plastic bag. Add chopped chipotle chiles and adobo sauce and dressing; seal bag. Turn bag to mix ingredients and coat drummettes. Refrigerate at least 4 hours but no longer than 24 hours, turning bag occasionally.
Heat oven to 425°F. Place sheet of foil in bottom of broiler pan. Arrange drummettes on foil. Bake 15 minutes; drain if necessary. Meanwhile, to make sauce, transfer marinade from bag to 2-quart saucepan; stir in caramel topping. Heat to boiling over medium-high heat; reduce heat to medium-low, and simmer.
Reduce oven temperature to 375°F; brush drummettes with sauce and bake about 30 minutes longer, brushing every 15 minutes with sauce, until browned and juice is clear when thickest part is cut to bone (180°F). Serve drummettes with sauce.