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Step 1
Finely grate 2 of the garlic cloves into a large bowl. Add 3 tablespoons of the olive oil, 3 tablespoons red wine vinegar, 2 tablespoons Italian seasoning, 1 1/2 teaspoons of the kosher salt, and 1 teaspoon of the black pepper. Whisk to combine.
Step 2
Working with 1 piece of chicken at a time, place 4 boneless, skinless chicken breasts in a large resealable bag and pound to an even 1/2-inch thickness. Add the chicken to the marinade and flip to coat. Cover and marinate at room temperature for 30 minutes or refrigerate for up to 2 hours.
Step 3
Meanwhile, finely grate the remaining 2 garlic cloves into a medium bowl. Add 2 teaspoons of the balsamic glaze and the remaining 2 tablespoons olive oil, 1/2 teaspoon kosher salt, and 1/2 teaspoon black pepper. Whisk to combine. Quarter 12 ounces cherry tomatoes. Pick the leaves from 4 fresh basil sprigs until you have about 1/4 cup and coarsely chop. Add both to the dressing and toss to combine. Refrigerate if marinating the chicken for longer than 30 minutes.
Step 4
Heat a 12-inch skillet or frying pan over medium-high heat until hot. Add the chicken in a single layer, shaking off any excess marinade back into the bowl. Sear until browned on the bottom, 5 to 7 minutes. Flip the chicken and continue cooking until the chicken is cooked through and registers at least 165ºF on an instant-read thermometer, 5 to 7 more minutes.
Step 5
Top the chicken evenly with 6 ounces sliced low-moisture mozzarella cheese, overlapping the slices as needed. Cover and cook until the mozzarella is melted, 1 to 2 minutes. Spoon the tomato mixture, including the juices, evenly over the chicken, allowing some tomatoes to fall to the bottom of the pan. Drizzle with the remaining 2 teaspoons balsamic glaze and remove the pan from the heat. Garnish with more chopped basil leaves if desired.