Set oven to broil. Brush both sides of chicken breasts with dressing. Sprinkle both sides with Italian seasoning and seasoned pepper. Place on rack in broiler pan.
Broil with tops 4 inches from heat about 10 minutes, turning once, until juice of chicken is clear when center of thickest part is cut (170°F). Top with tomato and cheese. Broil 2 to 3 minutes longer or until cheese is lightly browned.