Preheat your oven to 350 degrees. Spray a sheet pan with non-stick spray or line with foil.
Whisk together oil, vinegar, 1 clove garlic, and salt. Cover chicken with marinade.
Coat the butternut squash with 2 tbsp oil, and salt + pepper. Arrange chicken and butternut squash on a sheet pan.
Bake for 25-30 mins (depending on oven and thickness of chicken)
While chicken is baking, mix together tomatoes, basil, and remaining garlic (2 cloves).
Once chicken and squash are done baking, spoon tomato mixture over the chicken. Add additional drizzle of balsamic chicken if desired. Sprinkle with salt and pepper to taste.
Serve hot.