Place chicken in a large roasting pan coated with cooking spray. Brush chicken with 1 1/2 teaspoons olive oil; sprinkle with 1/4 teaspoon salt and 1/4 teaspoon pepper.
Place squash in a large bowl. Drizzle with remaining olive oil, and sprinkle with fine herbs, remaining salt, and remaining pepper; toss well. Add squash to pan. Bake at 450° for 38 minutes or until chicken is done. Transfer chicken and squash to a serving platter; keep warm.
Add wine to pan drippings; bring to a boil over high heat, scraping pan to loosen browned bits. Reduce heat; cook 2 minutes or until reduced to 1/4 cup. Place 1 chicken breast half on each of 4 plates. Spoon 1 tablespoon sauce over each chicken breast. Serve with squash.
Make it Faster
Peeling and cubing a butternut squash isn't difficult, but it will require a few extra minutes of your time. We peeled and cubed a butternut squash for this dish. To prepare this recipe even quicker, look for precubed butternut squash in the produce section of your supermarket. It may cost a little extra, but the trade-off is time saved in prepping this meal.