Butternut Squash Chili Delight

Butternut Squash Chili is a warm and smoky vegetarian dish that fills the kitchen with inviting aromas and offers a hearty comforting meal. Its combination of roasted butternut squash, smoky chipotles, and a blend of spices makes it both flavorful and satisfying in a single pot.

I first made this chili on a cool fall afternoon, and it quickly became a favorite in my home especially on evenings when we want something nourishing and meatless but still full of flavor

Ingredients

• Jalapeño peppers: roasted and peeled to add smoky mild heat
• Butternut squash: peeled and diced the star vegetable that provides natural sweetness and body
• Olive oil: split for roasting and sautéing ensuring layers of flavor and proper cooking technique
• Brown sugar: to balance the heat and acidity with a touch of sweetness
• Ground cinnamon: adds a warm spiced note that complements the squash beautifully
• Onion and GARLIC: finely chopped to build a rich savory foundation when cooked slowly
• Chipotles in adobo: bring smoky heat and complexity opt for mild to suit your spice preference
• Ground cumin and chili powder: for authentic chili flavor choose fresh spices for best aroma
• Dry red wine: helps deglaze the pan and deepens the flavor profile nicely
• Canned diced tomatoes and red kidney plus Cannellini beans: add texture protein and color
• Fresh oregano: brings herbal brightness to finish the chili
• Salt and pepper: to season carefully towards the end
• Optional toppings: like avocado and sour cream add creaminess and contrast

Instructions

Roast and peel peppers:

Preheat the broiler and position the rack a few inches below Cut jalapeños in half lengthwise and remove seeds Place skin side up on foil lined baking sheet Broil until the skin is evenly charred about one minute Immediately wrap in foil and let steam for five minutes to loosen the skin Peel carefully using hands or knife edge and finely chop Measure out a quarter cup and set aside

Prep and roast the squash:

Move the oven rack to the center and preheat to 475 degrees Fahrenheit Line a baking sheet with parchment paper Cut off the bottom and top of the squash for a stable base Using a sharp chef’s knife cut downward to peel the squash removing skin and seeds with a spoon Dice the flesh into roughly half inch chunks Toss them in a bowl with three tablespoons of olive oil brown sugar cinnamon and about three quarters teaspoon salt until evenly coated Spread on the prepared pan and roast for 20 minutes stirring or flipping halfway through to ensure even browning The squash should be golden and caramelized when done

Cook the onion and garlic:

While squash roasts heat remaining olive oil in a large Dutch oven or heavy stock pot over medium heat Add chopped onion and garlic cooking gently for about seven minutes until the onion begins to brown and soften This slow cooking unlocks sweetness and richness

Add peppers and spices:

Stir in the quarter cup of chopped roasted jalapeños chopped chipotles cumin and chili powder Cook together for about one minute until fragrant and the spices bloom releasing their aromas which builds the chili’s depth

Deglaze the pan:

Turn the heat to low and pour in the red wine scraping the pan gently to lift any flavorful bits stuck to the bottom Then bring the heat back up to medium high and cook until the wine reduces by half approximately four minutes This concentrates flavor and adds a subtle acidity

Add remaining ingredients and squash:

Pour in the canned diced tomatoes with their juices and drained kidney and Cannellini beans Add the roasted butternut squash and stir to combine Reduce the heat to low cover the pot slightly and simmer gently for 15 minutes to allow all the flavors to blend harmoniously

Season:

Stir in the fresh oregano and taste to adjust salt and pepper I typically add about one teaspoon of kosher salt but reduce the amount by half if using regular table salt Seasoning well at this stage ensures perfect flavor

Serve:

Serve with toppings such as diced avocado shredded cheddar red onion slices or a dollop of sour cream for contrast and creaminess if desired

One of my favorite parts of this recipe is roasting the jalapeños The smoky charred skins add an unexpected richness to the heat that canned chipotles alone don’t deliver This chili was a discovery at a family gathering one chilly fall where it stole the show and kept everyone coming back for seconds

Storage Tips

Store leftovers in an airtight container in the refrigerator for up to four days Reheat gently on the stove with a splash of water or broth to bring back moisture For longer storage freeze in portioned containers for up to three months Thaw in the fridge overnight before reheating

Ingredient Substitutions

You can swap jalapeños for a milder poblano pepper if you prefer less heat but still want a roasted flavor Dry white wine can be used instead of red for deglazing if that is what you have handy If fresh oregano is unavailable use dried oregano but add it earlier when you add the other spices to help it bloom Any type of canned beans can be substituted or mixed in according to your preference or pantry stock

Serving Suggestions

Serve with warm cornbread for a comforting classic pairing that soaks up the chili beautifully A simple green salad with a light vinaigrette offers a refreshing contrast to the richness Top with a squeeze of lime juice at the table to brighten and enhance the smoky flavors

This hearty butternut squash chili is perfect for cozy nights and makes great leftovers. Enjoy with your favorite toppings.

Common Questions About Recipes

→ How do you roast butternut squash for this dish?

Peel and dice the squash into ½-inch pieces, toss with olive oil, brown sugar, cinnamon, and salt, then roast at 475°F for about 20 minutes, flipping halfway through.

→ What is the purpose of roasting jalapeño peppers first?

Roasting and peeling jalapeños mellows their heat and adds a smoky depth that enhances the chili's flavor profile.

→ Can I substitute the red wine in the chili?

Yes, dry red wine adds richness but can be replaced with vegetable broth or omitted if preferred; just reduce the liquid accordingly.

→ How long should the chili simmer after adding all ingredients?

Simmer the chili on low heat, covered, for about 15 minutes to allow flavors to meld and squash to soften further.

→ What toppings complement the chili best?

Optional toppings like sliced avocado, shredded cheddar, chopped red onion, or sour cream add creaminess and contrast to the smoky flavors.