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On a clean work surface, halve each chicken breast horizontally (parallel to work surface) to make 8 (4-ounce) cutlets. For marinade, combine olive oil and dressing mix in a gallon-size resealable plastic bag. Add chicken; seal bag and turn to coat completely. Chill at least 1 hour or up to 8 hours.
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Meanwhile, for tomato salad, combine tomatoes, shallot, lemon juice, vinegar, basil, garlic, capers, salt, and pepper in a large bowl. Let stand at room temperature up to 1 hour before serving.
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Preheat an outdoor grill to medium heat (350 to 375 degrees F (175 to 190 degrees C)). Remove chicken from marinade; discard marinade.
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Oil grill grates. Arrange chicken on grill. Cook, covered, turning halfway through, until an instant-read thermometer inserted into thickest parts of chicken registers 165 degrees F (74 degrees C), 8 to 10 minutes. Serve chicken topped with tomato salad. Serve with Parmesan and lemon wedges.
Nutrition Facts (per serving)
301 Calories 11g Fat 14g Carbs 38g Protein