Cheesy Tomato Baked Skillet Chicken

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a simple & healthy cheesy tomato baked skillet chicken with a tangy olive topping

servings: 4


  • 4 boneless, skinless chicken breasts
  • kosher salt
  • freshly cracked black pepper
  • olive oil
  • 1 small red onion, thinly sliced
  • 1 small fennel bulb, thinly sliced
  • 4 cloves garlic, minced
  • ½ cup white wine
  • 1 (28 oz) can crushed tomatoes
  • ½ (16 oz) jar fire-roasted red peppers, drained + thinly sliced
  • 4 oz shredded mozzarella
  • 4 oz fresh mozzarella, sliced ¼”
  • grated parmesan cheese

for the olive topping (optional)…

  • ½ cup pitted, halved castelvetrano olives
  • 1 tbsp olive oil
  • 1 tbsp chopped fresh parsley
  • 1 tsp lemon zest


  1. Preheat the oven to 450°F. Pat the chicken dry and season well with salt and black pepper on both sides.
  2. Heat a 12” cast-iron skillet over medium-high heat. Add enough olive oil to coat the bottom. Once hot, place the chicken into the skillet. Sear on one side for about 3 minutes until golden brown. Flip and sear for another 2 minutes. Transfer the chicken out of the skillet and set aside.
  3. Turn the heat to medium. Add another drizzle of olive oil, plus the red onion and fennel. Season well and cook for about 6-8 minutes until caramelized, stirring often. Stir in the garlic. Cook for another 30 seconds.
  4. Pour in the white wine. Simmer for a minute or so. Stir in the roasted red peppers and crushed tomatoes. Bring the mixture to a simmer, reduce the heat to low, and gently simmer for 5 minutes.
  5. Place the chicken breasts back in the skillet, covering them with the sauce. Continue to simmer for another 5 minutes. Top the skillet with the shredded and sliced fresh mozzarella. Bake for about 8 minutes, or until the chicken is just cooked through. Turn the oven to high broil and broil the skillet for 2-3 minutes until the cheese is golden.
  6. Meanwhile, combine the olives, olive oil, parsley, and lemon zest in a small bowl. Mix well. Remove the skillet from the oven and let cool for a minute or so. Top with lots of grated parmesan cheese. Serve the olive topping alongside.


You can serve this chicken over pasta, with some crusty bread for dipping into the sauce, or just on its own!