Chicken Chili with Butternut Squash
This recipe completely redefines traditional chili by utilizing deeply savory ground chicken and aggressively roasting sweet, cinnamon-laced butternut squash separately in a blisteringly hot oven. Rather than simmering the squash down to mush, we build a heavy, intensely spiced tomato and bean foundation in a heavy Dutch oven, allowing those rich flavors to meld perfectly. The brilliant contrast arrives at the very end when the fiercely hot, savory chili is crowned with the caramelized, sweet squash chunks right in the serving bowl.
Serves: a crowd | Total Time: 40 minutes, plus simmering
Ingredients
For the butternut squash
- 1 medium butternut squash, peeled, seeded, and cut into 1-inch cubes, about 3 to 4 cups
- 2 tablespoons olive oil
- 1 tablespoon ground chili powder
- 1 teaspoon ground cinnamon
- 2 teaspoons kosher salt
- 2 teaspoons coarse black pepper
For the chili base and meats
- 3 tablespoons olive oil
- 2 large onions, peeled and diced into ½-inch pieces, about 3 cups
- 1 green bell pepper, seeded and cut into ½-inch pieces, about 1 cup
- 2 large jalapeño peppers, seeded, deveined, and finely diced, about ½ cup
- 6 to 8 garlic cloves, peeled and chopped, about ¼ cup
- 3 pounds ground chicken (a mixture of white and dark meat)
For the chili sauce and beans
- 3 tablespoons (or more) ground chili powder
- 2 tablespoons Worcestershire sauce
- 4 to 6 drops (or more) hot pepper sauce
- 2 (28-ounce) cans crushed tomatoes
- 1 (12-ounce) jar chili sauce
- 1 (6-ounce) can tomato paste
- 1 (15-ounce) can black beans, drained and rinsed
- 1 (15-ounce) can red kidney beans, drained and rinsed
Instructions
Roast the butternut squash
- Preheat your oven to 450°.
- Lay the butternut squash pieces on a baking sheet.
- Drizzle with 2 tablespoons olive oil.
- Sprinkle on 1 tablespoon ground chili powder and 1 teaspoon ground cinnamon.
- Season with some of the salt and pepper.
- Use your (very clean) hands to gently toss the squash in the seasonings.
- Roast until the squash is soft and beginning to turn golden, about 20 minutes. Remove from the oven.
Cook the chili
- Heat 2 more tablespoons olive oil in a large pot over medium-high heat.
- Add the onion, peppers, and garlic and cook until the veggies are soft and beginning to brown, about 8 to 10 minutes. Stir occasionally while cooking.
- Add another tablespoon olive oil to the pot.
- Add the ground chicken and cook, breaking up the clumps until the chicken is beginning to brown, about another 8 to 10 minutes.
- Generously season the chicken with salt, pepper, and 3 tablespoons chili powder. You can add more later if needed!
- Stir in Worcestershire and hot pepper sauce.
Simmer and serve
- Pour in crushed tomatoes and chili sauce.
- Stir in tomato paste.
- Add the beans.
- Reduce the temperature to low and simmer for 20 minutes.
- Stir, taste, and adjust the seasonings.
- Ladle the chili into bowls. Spoon roasted butternut squash on the top and dig in!
The full recipe lives in the Vault
Ingredients, step-by-step method, and every chef-tested detail are reserved for members of the Estate Registry.
Join the Estate RegistryThe Heart of the Table
Chili is the ultimate equalizer, instantly transforming a formal dining room into a relaxed, communal sanctuary. Setting down a massive, steaming cast-iron pot of this rich, dark red stew commands people to loosen their shoulders, lean in, and embrace the chaotic joy of a wildly unpretentious meal.
Neighborly Grace
- THE PRESENTATION: Serve this directly from a massive, deeply seasoned cast-iron Dutch oven placed squarely in the center of the table on a thick wooden trivet. Ladle the thick chili into wide, shallow ceramic bowls and spoon the bright orange, caramelized butternut squash directly on top right before handing it to your guests.
- THE POUR: The heavy chili powder and the sweet, earthy notes of the cinnamon squash require a beer with enough malt backbone to stand up to the spice without overwhelming the palate. An ice-cold, copper-hued Amber Ale or a deeply toasted Brown Ale is the undisputed champion here.
- THE VIBE: Effortlessly loud and unapologetically messy. This is the meal you prepare when the sun goes down early, the fire pit is roaring on the patio, and you want your guests to stay well past midnight.