Pat chicken breasts dry with paper towels to ensure pesto sticks well. Season lightly with salt and pepper for foundational flavor.
Generously spread pesto over both sides of each chicken piece to infuse herbaceous richness.
Place chicken breasts spaced apart in the air fryer basket. Scatter cherry tomatoes around chicken, then drizzle olive oil over all to promote roasting.
Air fry at 375°F (190°C) for about 15-18 minutes, flipping chicken halfway through. Check tomatoes for blistering and chicken for doneness.
Use a meat thermometer to ensure chicken reaches 165°F (74°C), guaranteeing safety and juiciness without overcooking.
Let chicken rest a few minutes after cooking to redistribute juices. Garnish with fresh basil or a squeeze of lemon juice before serving if desired.