Hearty Butternut Squash Chili

This hearty butternut squash chili brings together smoky flavors, warming spices, and comforting vegetables in one satisfying vegetarian dish. It’s built to be a filling onepot meal perfect for chilly evenings, blending sweetness from roasted squash with a gentle heat from jalapeños and chipotles.

This recipe quickly became a favorite after I made it for a casual family dinner. It was so warmly received that it has become a go to anytime I want something both comforting and nutritious.

Ingredients

• Roasted and peeled jalapeño peppers: Four ounces for a smoky mild heat roasting and peeling intensifies their flavor and softens the bite
• Butternut squash: Two and a half pounds peeled and diced which adds natural sweetness and a creamy texture when roasted
• Olive oil: Quarter cup divided to coat the squash for caramelizing and to sauté aromatics
• Brown sugar: To complement the squash's natural sweetness and enhance caramelization
• Ground cinnamon: Adds warmth and a subtle earthy depth
• Onion: One cup finely chopped for a savory base and sweetness when cooked down
• Garlic: One teaspoon minced for pungency and flavor complexity
• Chipotles in adobo sauce: Finely chopped to contribute a smoky spiciness
• Ground cumin and mild chili powder: Create the classic chili flavor profile
• Dry red wine: Half a cup to deglaze the pan and concentrate the aromatics
• Diced tomatoes: One 28 ounce can in their juices to add acidity and structure into the chili
• Red kidney beans and Cannellini beans: One 15 ounce can each for heartiness and protein
• Fresh oregano: One and a half tablespoons chopped for a herbal brightness
• Salt and pepper: To taste
• Optional toppings: Avocado, cheddar cheese, red onion, and sour cream to add creaminess and texture contrast

Instructions

Roast and peel peppers:

Turn on the broiler and position a rack a few inches from the heat Cut jalapeños in half lengthwise and remove seeds Place them on a foil lined baking sheet cut side up broil until skins are evenly charred about one minute Remove from heat and loosely wrap in the foil letting them steam for five minutes Peel off skins using your hands or the back of a knife then finely chop the flesh and measure out a quarter cup Set aside

Prep and roast the squash:

Preheat the oven to 475 degrees Fahrenheit with a rack in the middle Line a sheet pan with parchment paper Trim off the ends of the butternut squash and peel the skin by slicing downward with a sharp knife removing seeds with a spoon Cut squash into quarter to half inch dice and toss in a bowl with three tablespoons of olive oil brown sugar cinnamon and about three quarters teaspoon of salt until well coated Spread the squash evenly on the parchment lined sheet pan and roast for about 20 minutes stirring or flipping halfway through until golden brown

Cook the onion and garlic:

While the squash roasts heat the remaining olive oil in a large Dutch oven or stockpot over medium heat Add the chopped onion and garlic cooking gently until the onions start to brown and caramelize about seven minutes building a deep flavor base for the chili

Add peppers and spices:

Stir in the roasted chopped jalapeños along with chipotles cumin and chili powder Cook until fragrant about one minute letting the spices bloom in the oil

Deglaze the pan:

Lower the heat and pour in the red wine increase to medium high Simmer until the wine reduces by about half concentrating the flavors around four minutes

Combine remaining ingredients and simmer:

Add diced tomatoes with their juices both kinds of drained beans and the roasted squash Lower heat to a gentle simmer cover and cook for 15 minutes to allow flavors to meld beautifully

Season and serve:

Stir in chopped oregano and season with salt and pepper to taste Typically one teaspoon of kosher salt works well reduce if using table salt Serve with your choice of optional toppings such as sliced avocado shredded cheddar diced red onion or sour cream for extra richness and texture contrast

I have a special fondness for the roasted butternut squash here Roasting transforms the squash from mild and starchy to tender with a caramelized exterior that adds a lovely textural contrast to the creamy beans One winter evening when the power went out this chili was my saving grace as the oven could still be used intermittently and the warm bowl brought instant comfort to everyone gathered around.

Storage Tips

Cool the chili completely before transferring it to an airtight container It will keep in the refrigerator for up to four days Reheat gently on the stovetop or in the microwave stirring occasionally to keep it smooth

Ingredient Substitutions

If you cannot find chipotles in adobo smoked paprika can add a milder smoky note Black beans can stand in for kidney beans if preferred For a spicier kick add extra jalapeños or a pinch of cayenne powder in step five

Serving Suggestions

This chili pairs beautifully with crusty cornbread or over a bed of fluffy rice A side salad with fresh greens and a citrusy dressing lightens the meal and cuts through the richness

This butternut squash chili is hearty and perfect for cozy dinners. It freezes well and reheats beautifully.

Your Recipe Questions Answered

→ How should the jalapeño peppers be prepared for the best flavor?

Roast and peel the jalapeño peppers under the broiler until charred, then steam in foil to loosen skins before finely chopping. This adds a smoky depth to the chili.

→ Can I substitute the red wine used in cooking?

Yes, you can replace red wine with a non-alcoholic alternative like vegetable broth or grape juice to maintain moisture and acidity without alcohol.

→ What is the best way to roast butternut squash evenly?

Cut into uniform ½-inch dice, coat with oil, brown sugar, and cinnamon, then roast on a parchment-lined pan at 475°F, turning halfway for golden brown edges.

→ How can I adjust the chili's heat level?

Modify the amount of roasted jalapeños and chipotles in adobo sauce. Removing seeds reduces heat, while adding more peppers increases spiciness.

→ What toppings complement this smoky chili?

Avocado slices, shredded cheddar, diced red onions, and a dollop of sour cream add creamy, tangy contrasts to the rich, smoky flavors.

→ Is this chili suitable for leftovers?

Yes, flavors deepen overnight when refrigerated. Reheat gently on the stove or microwave, adding a splash of water if needed.