01 - Preheat grill pan or skillet over medium-high heat. Brush chicken breasts with olive oil and season with salt and black pepper.
02 - Grill chicken for 6 to 7 minutes per side until fully cooked and juices run clear. Let rest for 5 minutes, then slice into thin strips.
03 - Combine chopped romaine lettuce with Caesar dressing in a large bowl and toss until evenly coated.
04 - Place tortillas flat. Distribute dressed lettuce, sliced chicken, shaved Parmesan, cherry tomatoes (if using), and crushed croutons evenly among tortillas.
05 - Fold sides of each tortilla inward and roll tightly like a burrito.
06 - Slice wraps diagonally in half and serve immediately.