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Butternut Squash Chili -- Like a Boss

Updated: Jan 16, 2023

In 2014, I published a chili recipe on my first blog (iConveyAwareness) which is a big hit in my home. When I casually mention the recipe title, "Chili Like a Boss," my family knows exactly which dish I'm talking about!

Since I have a teen son, I am doubling all of my recipes. One batch doesn't cut it anymore. Sometimes two is too much but the freezer is a solution!

This recipe can be made with vegetarian options - no animal protein. The chili is gluten-free and can be made dairy-free when sour cream (or plain greek yogurt) and shredded cheese (not pictured) are omitted.

There are a lot of ingredients in this chili and you can add or subtract where you see fit. I know that it will still come out delish! I did not use any pre-made spice/chili packets but I did resort to using some ingredients from a can. (I limit canned goods due to BPA in the lining - some brands have none.) I have yet to master beans from dried. I always use canned beans.

Does the act of peeling a butternut squash scare you? It did me until I decided to roast the vegetable to soften the outer skin. To do so, preheat the oven to 325°. Cut an inch off both ends and scoop the seeds out. (You do not need to slice it down the center vertically unless you want to. Be careful cutting.) Place in a shallow pan with water and roast for about 30 minutes. (If you cut it down the center, you'll need less time in the oven. Start with half the time and adjust as necessary.) Note: You do not want to roast too long as the squash itself will be mushy and it may not hold up in the chili. You will know it's ready to peel when you see that the skin is wrinkling in the oven. You can also stick a fork in the center to sense its firmness.

Double the ingredients for extra portions for a growing family. If you find you made too much, you can freeze the leftovers. After the chili is cool (or has been refrigerated), it can be frozen in a container for the freezer. You can also pour a serving into a single-serve container and then freeze it. Let thaw in the fridge then heat in a pot on the stove or in the microwave.


2 T olive oil (I use EVOO)

1 medium onion, diced

2-5 garlic cloves minced (use more or less)

1-3 medium bell peppers (orange/yellow/red), diced

4 cups of vegetable broth/stock (DIY here)

1/2 can of diced tomatoes with green chilis

1 butternut squash, cut, cleaned, peeled, and chopped into 1/2-inch pieces

1 lb ground turkey, browned and oil drained

1 T olive oil

2 tsp cumin

2 tsp dried oregano

1 tsp paprika (can omit, I like to use paprika when cooking turkey to give it a more appealing look)

1- 14 oz diced tomatoes (plain)

1- 8 oz can of tomato sauce

1- 8 oz can of black beans, drained and rinsed

1 cup corn (frozen, fresh off the cob, or canned)

2 tsp chili pepper (can omit if the tomatoes with chilis will make it spicy enough)

Optional toppings:

Plain Greek yogurt (or sour cream)

Shredded cheese


Tortilla chips (on the side for dipping)


1. Preheat oven to 325° and prepare the butternut squash for roasting. (See notes above.) I recommend doing this step ahead of preparing the other ingredients. This way the vegetable will be cool enough to peel and chop so that you can add this ingredient in step 8.

2. While squash is roasting: In a large soup pot (about 6 quarts), brown the diced onions in the 2 tablespoons of olive oil on medium heat.

3. While onions are browning: In a skillet, brown the ground turkey. Add cumin, oregano, and paprika. You can also add minced garlic here too. Having a good garlic press makes all the difference. After having one for many years, I ended up buying this one by OXO. I like that it has a self-cleaning tool built in and you can press several cloves at once. The previous press I had started to peel - yuck! (I earn affiliate commission on linked products from Amazon.) When done, drain the oil, and set aside for step 9.

4. Add chopped bell peppers as the onions are softening.

5. When onions are brown and bell peppers are fragrant, add the 2-3 garlic cloves. Cook for 1 minute.

6. Add 2 cups of vegetable broth and bring to a simmer. About 5 minutes.

7. Add tomatoes - diced, with chilis, and sauce.

8. Add chopped butternut squash. Add the remaining broth here. If you want more liquid, you may opt for additional broth (or water works fine here as well).

9. Add the ground turkey. Give it a good stir.

10. Add in corn. Stir.

11. Add the chili pepper and any remaining cumin, oregano, and garlic. Stir.

12. Cover and cook on medium-low until the squash is the texture you like. Stir occasionally. I cooked mine for 30 minutes. Turn off the heat.

When ready to eat, serve. Be careful it may be hot. Add toppings if you so desire. Tortilla chips are great with this chili.

The Chili Like a Boss can stand alone -- no problem! It is filling and packs flavor without too much heat (spice). When I first made this recipe, my son was 5 and it was satisfying for him. He has grown up with me serving/offering vegetables (and fruit) at every meal since he was a baby. This is a far cry from how I was raised. Every generation can make small changes that create long-lasting ripple effects.

Choose, eat, and live well! =)


I'm not an RD or Nutritionist, so if you're concerned about ingredients or calories/fat content, be sure to read the labels and choose foods that align with your preferences and dietary needs. If this recipe sounds good to you, give it a try, and tell me about it. I'd love to hear about your experience! #goodeats

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© Conveying Awareness with Jessica David

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