Set an oven rack about 6 inches from the heat source and preheat the oven's broiler.
Combine olive oil and red pepper flakes. Place asparagus on a baking sheet and drizzle olive oil mixture over top; mix together with your hands to coat.
Cut each slice of prosciutto in half lengthwise. Wrap a strip of prosciutto around each asparagus spear, angling as you wrap to cover most of the asparagus. Arrange on the baking sheet and season with salt and pepper.
Broil in the preheated oven until prosciutto is sizzling and crispy and asparagus is tender, 5 to 7 minutes.
Transfer asparagus to a serving platter. Drizzle with balsamic vinegar and serve immediately.