Cut chicken into 1-inch cubes.
Place the cubed chicken in a large, resealable plastic bag with the chimichurri. Work the bag so that chicken is completely coated.
Thread chicken on metal skewers.
Grease fryer basket with 2 teaspoons olive oil.
Preheat air fryer to 400 degrees.
Place skewers in the basket, and cook for 6 minutes.
Toss the tomatoes with remaining olive oil, salt, and pepper.
Place the tomatoes in the air fryer, and flip the chicken skewers.
Cook for an additional 5 minutes, or until chicken registers165 degrees with a meat thermometer.
Serve chicken with tomatoes and extra chimichurri for dipping.