Gather and prep all ingredients. Preheat your air fryer to 350°F (175°C).

Toss the asparagus spears with olive oil, garlic powder, onion powder, salt, and pepper. Set aside.

Lay the chicken breast flat on a cutting board. Carefully cut a deep pocket into the side of each breast.

In a small bowl, combine cream cheese, pesto, grated parmesan cheese, salt, and pepper. Mix until smooth.

Spoon the cream cheese mixture into the pockets of each chicken breast.

Drizzle olive oil over the stuffed chicken breasts and season the outside with salt and pepper.

Arrange the seasoned asparagus in the air fryer basket. Place the stuffed chicken on top.

Air fry for 18-22 minutes, or until the chicken is cooked through and the asparagus is tender-crisp.