Quick Recipe Version (TL;DR)
Quick Ingredients
- 1 medium butternut squash (2.5–3 lb), peeled and cubed (about 6 cups)
- 3 tbsp olive oil, divided
- 1½ lb mild Italian sausage (bulk or casings removed)
- 1 large yellow onion, diced
- 1 red bell pepper, diced
- 4 garlic cloves, minced
- 1 tbsp fresh sage, finely chopped (or 1½ tsp dried rubbed sage)
- 1 tsp chili powder
- 1 tsp smoked paprika
- ½ tsp ground cumin
- 1 (28-oz) can crushed tomatoes (fire-roasted if possible)
- 1 (4-oz) can mild diced green chiles
- 1½ cups low-sodium chicken broth
- 2 (15-oz) cans cannellini or Great Northern beans, drained and rinsed
- Salt and freshly ground black pepper
- Optional toppings: Greek yogurt or sour cream, shredded sharp cheddar, sliced green onions, extra sage
Do This
- 1. Heat oven to 400°F (200°C). Toss squash cubes with 2 tbsp olive oil, salt, and pepper; roast 25–30 minutes, flipping once, until tender and caramelized at the edges.
- 2. While squash roasts, brown sausage in a large pot over medium-high heat, breaking it into crumbles, about 7–9 minutes. Spoon off excess fat if needed.
- 3. Add remaining 1 tbsp olive oil, onion, and bell pepper; cook until softened, 5–7 minutes. Stir in garlic and sage; cook 1 minute.
- 4. Add chili powder, smoked paprika, cumin, salt, and pepper; toast 30 seconds. Stir in crushed tomatoes, green chiles, and chicken broth; bring to a simmer.
- 5. Add beans, reduce heat to low, and simmer gently 20–25 minutes, stirring occasionally, until thickened and flavorful.
- 6. Gently fold in roasted squash and simmer 5 minutes more to warm through. Taste and adjust seasoning.
- 7. Serve in warm bowls with a dollop of yogurt or sour cream, shredded cheddar, sliced green onions, and extra sage, if desired.
Why You’ll Love This Recipe
- Cozy fall flavors: sweet roasted butternut squash meets savory sage sausage in a rich, tomato-chile broth.
- Hearty but not heavy: white beans add creaminess and protein without making the chili greasy.
- Make-ahead friendly: tastes even better the next day and freezes beautifully.
- Flexible heat level: keep it mellow and family-friendly or amp up the spice easily.
Grocery List
- Produce: 1 butternut squash, 1 large yellow onion, 1 red bell pepper, 4 garlic cloves, fresh sage, green onions (for garnish, optional)
- Dairy: Greek yogurt or sour cream, sharp cheddar cheese (for garnish, optional)
- Pantry: Olive oil, salt, black pepper, chili powder, smoked paprika, ground cumin, 1 (28-oz) can crushed tomatoes, 1 (4-oz) can mild diced green chiles, 2 (15-oz) cans white beans (cannellini or Great Northern), low-sodium chicken broth
- Meat: 1½ lb mild Italian sausage (or other pork sausage)
Full Ingredients
For the Roasted Squash
- 1 medium butternut squash (about 2.5–3 lb), peeled, seeded, and cut into ¾-inch cubes (about 6 cups)
- 2 tbsp olive oil
- ½ tsp fine sea salt
- ¼ tsp freshly ground black pepper
For the Chili
- 1½ lb mild Italian sausage, bulk or casings removed
- 1 tbsp olive oil (plus more only if needed)
- 1 large yellow onion, diced (about 2 cups)
- 1 red bell pepper, diced
- 4 garlic cloves, minced
- 1 tbsp fresh sage leaves, finely chopped (or 1½ tsp dried rubbed sage)
- 1 tsp chili powder
- 1 tsp smoked paprika
- ½ tsp ground cumin
- 1 tsp fine sea salt, plus more to taste
- ½ tsp freshly ground black pepper, plus more to taste
- 1 (28-oz) can crushed tomatoes (fire-roasted if available)
- 1 (4-oz) can mild diced green chiles, undrained
- 1½ cups low-sodium chicken broth (or vegetable broth)
- 2 (15-oz) cans cannellini or Great Northern beans, drained and rinsed
Optional Add-Ins
- 2 cups chopped kale or baby spinach, loosely packed (stirred in at the end)
- Pinch of red pepper flakes, for extra heat
- ½ tsp brown sugar or maple syrup if your tomatoes taste very acidic
For Serving
- Plain Greek yogurt or sour cream
- Shredded sharp cheddar or aged white cheddar
- Thinly sliced green onions or chives
- Extra fresh sage leaves, finely chopped
- Crusty bread or warm cornbread (optional, for serving alongside)
Step-by-Step Instructions
Step 1: Prep and Roast the Butternut Squash
Preheat your oven to 400°F (200°C). Line a large rimmed baking sheet with parchment paper for easy cleanup. Peel the butternut squash, cut it in half lengthwise, and scoop out the seeds. Cut the flesh into roughly ¾-inch cubes so they cook evenly.
Place the squash cubes on the baking sheet. Drizzle with 2 tablespoons olive oil, then sprinkle with ½ teaspoon salt and ¼ teaspoon black pepper. Toss well to coat and spread into a single layer without crowding (use two pans if needed so the squash roasts instead of steams).
Roast for 25–30 minutes, flipping once halfway through, until the cubes are tender and browned in spots with lightly caramelized edges. Set aside while you start the chili.
Step 2: Brown the Sage Sausage
While the squash roasts, heat a large heavy-bottomed pot or Dutch oven over medium-high heat. Add the sausage (no oil yet) and cook, breaking it into small crumbles with a wooden spoon, until cooked through and nicely browned, about 7–9 minutes.
If there is more than about 1–2 tablespoons of fat in the pot, carefully spoon off the excess, leaving enough to flavor the aromatics. If your sausage is very lean and the pot looks dry, add up to 1 tablespoon of olive oil to keep things from sticking.
Step 3: Soften the Aromatics
Reduce the heat to medium. Add 1 tablespoon olive oil (if not already added), then stir in the diced onion and red bell pepper. Cook, stirring occasionally, until the onion is translucent and the pepper has softened, 5–7 minutes.
Add the minced garlic and chopped fresh sage. Cook, stirring constantly, for about 1 minute, just until fragrant. This blooms the garlic and sage flavor without letting them burn.
Step 4: Build the Flavor Base
Sprinkle in the chili powder, smoked paprika, ground cumin, 1 teaspoon salt, and ½ teaspoon black pepper. Stir well to coat the sausage and vegetables in the spices, and cook for 30–60 seconds. This quick toasting step wakes up the dried spices and deepens the flavor of the chili.
Pour in the crushed tomatoes, diced green chiles (with their juices), and chicken broth. Stir well, scraping up any browned bits from the bottom of the pot. Those browned bits add a lot of savory flavor.
Step 5: Add the Beans and Simmer
Stir in the drained and rinsed beans. Bring the mixture just up to a boil over medium heat, then immediately reduce the heat to low so the chili is at a gentle simmer. Partially cover the pot with a lid, leaving it slightly ajar.
Simmer for 20–25 minutes, stirring occasionally, until the chili has thickened slightly and the flavors have melded. If at any point it seems too thick for your liking, splash in a little extra broth or water (about ¼ cup at a time).
Step 6: Fold in the Roasted Squash and Greens
Once the chili base tastes rich and cozy, gently add the roasted butternut squash cubes to the pot. Stir carefully so you do not completely mash the squash; it is fine if a few edges break down a bit, as that helps thicken the chili.
If you are using kale or spinach, stir it in now as well. Simmer for another 5 minutes, just to warm the squash through and lightly wilt any greens. Taste and adjust the seasoning with more salt and pepper as needed. If the tomatoes taste very sharp, stir in up to ½ teaspoon brown sugar or a drizzle of maple syrup to balance the acidity.
Step 7: Serve and Garnish
When the chili tastes balanced and the squash is hot all the way through, turn off the heat. Ladle the chili into warm bowls. Top each serving with a spoonful of Greek yogurt or sour cream, a small handful of shredded cheddar, and a sprinkle of sliced green onions and chopped fresh sage.
Serve hot, ideally with crusty bread or cornbread on the side for dipping. The chili will continue to thicken slightly as it sits, so you can loosen leftovers with a splash of broth or water when reheating if needed.
Pro Tips
- Roast the squash hot: A 400°F (200°C) oven ensures caramelized edges and concentrated sweetness, which makes the chili taste deeper and more complex.
- Brown the sausage well: Let it sit undisturbed for a minute or two at a time so it develops color. Those browned bits are flavor gold.
- Control the thickness: For a thicker, stew-like chili, simmer uncovered for the last 10 minutes. For a looser, more brothy bowl, add a bit more broth.
- Add squash at the end: Stir the roasted squash in during the last few minutes so it holds its shape and does not turn mushy.
- Adjust the heat level: The recipe is quite mild as written. For more kick, add red pepper flakes or use medium diced green chiles instead of mild.
Variations
- Vegetarian version: Swap the sausage for a plant-based sausage or 1 additional can of white beans plus 1 can of chickpeas. Use vegetable broth and add an extra ½ teaspoon smoked paprika for savory depth.
- Spicier chili: Use hot Italian sausage, add ½ teaspoon red pepper flakes with the spices, and choose medium or hot diced green chiles. You can also finish with a dash of hot sauce.
- Different squash or beans: Try kabocha or delicata squash instead of butternut, or substitute navy beans or pinto beans if that is what you have on hand.
Storage & Make-Ahead
Let the chili cool to room temperature, then transfer it to airtight containers. Refrigerate for up to 4 days. The flavors actually improve overnight, making this an excellent make-ahead meal. To freeze, portion the cooled chili into freezer-safe containers or zip-top bags, leaving a little room for expansion, and freeze for up to 3 months.
Reheat gently on the stovetop over medium-low heat or in the microwave, adding a splash of water or broth if it has thickened too much. If you plan to freeze the chili, you can slightly undercook the squash so it holds its shape better after thawing and reheating.
Nutrition (per serving)
Approximate values for 1 of 6 servings (without toppings): about 520 calories, 28 g protein, 24 g fat, 44 g carbohydrates, 10 g fiber, and 1150 mg sodium. Toppings like cheese and sour cream will add additional calories and fat. Use reduced-sodium broth and sausage if you are watching your sodium intake.
