Preheat oven to 450 degrees F. Combine chicken, 2 tbsp of olive oil, vinegar, garlic, herbs, salt, and pepper into a zip-lock bag and set aside. Place sweet potato, squash, brussels sprouts, apples, and onion on a large rimmed baking sheet. Drizzle the chopped fruit and vegetables with 2 tbsp of olive and toss well to evenly coat. Season with salt and pepper to taste. Set the chicken on top of the fruit and vegetables.