Season the chicken breasts with salt and pepper. In a skillet, heat olive oil over medium-high heat. Cook the chicken for about 5 minutes on each side until golden brown and cooked through. Let it cool slightly, then slice into small pieces.
Warm the tortillas in a skillet or microwave briefly to make them pliable.
Spread a layer of Caesar dressing over each tortilla. Sprinkle the chopped tomatoes evenly over the chicken. Sprinkle grated Parmesan cheese and add the crushed croutons for crunch.
Carefully roll each tortilla, tucking in the sides to form a wrap. Slice the wraps in half diagonally and serve with lemon wedges and extra Caesar dressing on the side.