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In a plastic resealable bag, whisk together 1/4 cup olive oil, red wine vinegar, garlic, Italian seasoning, and lemon juice. Add chicken breasts to the bag and seal. Turn to coat. Allow to marinate for at least 30 minutes, turning occasionally.
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Meanwhile, prepare the herb dressing and the rest of your bowl ingredients. Combine garlic, egg yolk, red wine vinegar, cilantro, parsley, and basil in a food processor until finely chopped and combined. With food processor running, slowly stream in olive oil and allow to run until creamy and smooth. Season with salt and pepper to taste.
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Heat a large cast iron skillet or grill pan over medium-high heat. Add remaining tablespoon of olive oil to the pan and heat. Season chicken on both sides with kosher salt and cook, about 3-4 minutes per side. Remove chicken to a cutting board and allow to rest for 5-10 minutes before slicing.
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In a large bowl, combine kale, red onion, quinoa, and cranberries. Toss to combine. Serve salad topped with sliced chicken and creamy herb dressing.