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Preheat the oven to 425 degrees F (220 degrees C). Line a large baking sheet with aluminum foil. Place chicken and potatoes in a large bowl.
Whisk ¼ cup olive oil, balsamic vinegar, Dijon mustard, paprika, oregano, garlic, black pepper, and chili flakes together in a small bowl. Pour mixture over chicken and potatoes; toss to coat. Arrange chicken and potatoes on the prepared baking sheet in an even layer.
Bake in the preheated oven until chicken juices run clear and potatoes are tender, 30 to 35 minutes. An instant-read thermometer inserted near the center of chicken should read 165 degrees F (74 degrees C).
Meanwhile, for brine, stir 2 tablespoons olive oil, olives, lemon juice, pepperoncini, basil, and dill together in a small bowl. Stir tzatziki sauce and feta together in a separate bowl.
Remove chicken and potatoes from the oven. Divide onto serving plates. Drizzle with olive brine and top with tzatziki feta sauce. Serve immediately.