Preheat the grill to medium-high heat.
In a small bowl, mix together olive oil, garlic powder, Italian seasoning, salt, and pepper. Brush the mixture over both sides of the chicken breasts.
Place the chicken on the grill and cook for about 6-7 minutes per side, or until the internal temperature reaches 165°F. Remove from the grill and let rest for 5 minutes before slicing.
In a large bowl, combine the chopped romaine lettuce, cherry tomatoes, Caesar dressing, and half of the Parmesan cheese. Toss well to coat the lettuce evenly.
Divide the salad mixture among four plates. Top each salad with sliced grilled chicken, remaining Parmesan cheese, and croutons.
Serve immediately and enjoy!