Butternut Squash Chili (Ready-to-Print Version)

Smoky chili with roasted butternut squash, jalapeños, beans, and warming spices for a deliciously hearty meal.

# What You’ll Need:

→ Produce

01 - 4 ounces roasted, peeled, finely chopped jalapeño peppers (approximately 4 small peppers, yielding ¼ cup)
02 - 2½ pounds butternut squash, peeled and diced into ½-inch pieces (approximately 4 cups)
03 - 1 cup finely chopped onion
04 - 1 teaspoon minced garlic
05 - 1½ tablespoons finely chopped fresh oregano, washed and dried

→ Pantry

06 - ¼ cup olive oil, divided
07 - 1 tablespoon brown sugar
08 - 1 teaspoon ground cinnamon
09 - 1 teaspoon finely chopped chipotles in adobo sauce
10 - 1½ teaspoons ground cumin
11 - 1 tablespoon mild chili powder
12 - ½ cup dry red wine (Cabernet, Merlot or Shiraz)
13 - 1 (28-ounce) can diced tomatoes in juices
14 - 1 (15-ounce) can red kidney beans, drained
15 - 1 (15-ounce) can Cannellini beans, drained
16 - Salt and pepper, to taste

# Step-by-Step Guide:

01 - Preheat broiler and position rack a few inches below it. Halve jalapeños lengthwise and remove seeds. Place skin side up on foil-lined baking sheet and broil until skin is evenly charred, about 1 minute. Remove, wrap loosely in foil, and steam for 5 minutes. Peel off skins and finely chop. Measure out ¼ cup and set aside.
02 - Preheat oven to 475°F with rack centered. Peel the squash by slicing downward between skin and flesh after trimming ends. Remove seeds with a spoon. Dice into ¼ to ½-inch pieces. Toss in a bowl with 3 tablespoons olive oil, brown sugar, cinnamon, and ¾ teaspoon salt until evenly coated. Spread on parchment-lined sheet pan and roast for 20 minutes, stirring halfway until golden brown.
03 - Heat remaining olive oil in a 5-quart Dutch oven over medium heat. Add onion and garlic, cooking until onion begins to brown, about 7 minutes.
04 - Add the chopped jalapeños, chipotles in adobo, cumin, and chili powder to the pot. Cook until fragrant, approximately 1 minute.
05 - Reduce heat to low and pour in the red wine. Increase heat to medium-high and simmer until the wine reduces by half, about 4 minutes.
06 - Add diced tomatoes with juices, drained kidney beans, Cannellini beans, and roasted butternut squash. Lower heat, cover, and simmer gently for 15 minutes to meld flavors.
07 - Stir in fresh oregano and season with salt and pepper to taste (approximately 1 teaspoon kosher salt or half as much table salt). Serve warm, optionally topped with avocado, shredded cheddar cheese, diced red onion, or sour cream.

# Handy Tips:

01 - Use kosher salt for seasoning or adjust amounts when substituting with table salt for balanced flavor.

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