Heat olive oil in a large skillet over medium-high heat. Season chicken pieces with salt and pepper, then brown them for 3-4 minutes per side. This creates a flavorful crust while the interior stays juicy.
Remove chicken and set aside on a clean plate. Add diced onion to the skillet and sauté for 2 minutes until fragrant and softened slightly.
Stir in minced garlic, cooking for just 30 seconds until aromatic. Pour in chicken broth, scraping up any browned bits from the skillet bottom for maximum flavor depth.
Add butternut squash, mushrooms, apples, thyme, and sage to the broth mixture. Return the cozy fall chicken skillet dinner to the pan, nestling pieces into the liquid for even cooking.
Simmer for 15-18 minutes until the squash is tender and chicken reaches 165°F internally. The vegetables should be soft enough to cut easily with a fork.
Reduce heat to low and stir in butter and heavy cream until fully combined. Taste and adjust seasonings as needed—this step takes just 2 minutes.
Garnish with fresh parsley and serve immediately while steam rises from the skillet. The aroma alone will have everyone gathering around the kitchen.