Chili Stuffed Acorn Squash

Move over, chili in a bread bowl, there’s a better idea in town – Chili Stuffed Acorn Squash! You get all the fun of digging your favorite chili out of an edible bowl, only this version is veggie-packed and naturally gluten free. Plus, the sweetness of the roasted acorn squash is irresistible with spicy flavor, making this a hearty and tasty dinner for a cold night.
Love this idea? Then try Italian Ground Beef Stuffed Acorn Squash!

Delicious Details
- Cuisine Inspiration: American
- Primary Cooking Method: Oven
- Dietary Info: Gluten-free, Dairy-free option
- Skill Level: Easy
Of course, stuffing one of your favorite chili recipes inside a gluten free bread bowl is the epitome of comfort food. But prepare to be blown away when your hearty, smoky, and spicy chili is balanced with the tender, subtly sweet, earthy flavor of roasted acorn squash. Chili Stuffed Acorn Squash is the combo you never knew you needed, and you won’t believe how fun and tasty it is to enjoy this veggie-packed chili bowl you can eat!
What You’ll Need for Chili Stuffed Acorn Squash
Here’s a quick overview of the ingredients and options to make this recipe. Just below is the full recipe card with ingredient amounts and step-by-step instructions.
- Acorn Squash. You’ll need one squash for every two servings. Just cut it in half, lightly coat it with olive oil, salt, and pepper, then toss it in the oven.
- Chili. I like to make these acorn squash chili bowls after I’ve made a big pot of the World’s Best Chili because it makes so much that I always have leftovers. But if you need to whip up something fast, try my Quick Ground Turkey Chili. You can also make No-Bean Chili, or pop some Slow Cooker Hawaiian Chili in your crockpot in the morning. Also, feel free to use your favorite recipe or, in a pinch, canned chili – there are several brands that are gluten free if that’s a concern for you.
- Cheese. I always like to pop my squash back in the oven with a topping of shredded sharp cheddar to let it melt. You can use your favorite, like pepper Jack or even some cheese sauce. Also, feel free to omit it for a dairy free dish.
- Toppings. This is where you can get creative. I’m partial to sour cream or Greek yogurt and avocado. But many folks also like raw onion, cilantro, tortilla chips, and more!

Make it a Meal
- Have some bread. If you just can’t have your chili without a carby side, then bake some Gluten Free Cornbread, or whip up garlicky Gluten Free Texas Toast.
- Toss a salad. Combine your favorite greens and veggies with a drizzle of BBQ Ranch Dressing or Red Wine Vinaigrette.
- Serve with slaw. Whether on the side or on top, a crisp, cool coleslaw is a nice contrast, so try a scoop of Taco Slaw or Pineapple Coleslaw.
More Stuffed Veggie Recipes

Chili Stuffed Acorn Squash
Ingredients
- 2 large acorn squash
- 1 tsp olive oil
- salt and pepper
- your favorite chili (about 4 cups)
- 1 cup shredded cheddar cheese (about 4 oz.)
- sour cream or Greek yogurt, avocado, tortilla chips, or your favorite chili toppings
Instructions
- Preheat oven to 400°F. Coat a baking sheet with olive oil; set aside.
- Cut 2 large acorn squash in half, then scoop out and discard the seeds. Brush the cut halves with 1 tsp olive oil, then sprinkle with salt and pepper. Roast the squash cut side down until tender, about 20-25 minutes.
- Fill each squash half with your favorite chili, about 1 cup in each, and top with 1 cup shredded cheddar cheese. Return to the oven for 5-7 minutes, or until cheese is melted and slightly browned.
- Serve with sour cream or Greek yogurt, avocado, tortilla chips, or any other toppings, as desired.




Oh wow! That looks amazing!!!
Yay!! I love being a sports mom : ) It really is so much fun to watch our kids play their hearts out!!
This recipe looks incredible! I have to check out those McCormick skillet sauce mixes…this is my kind of dinner!!
So from now on we get to call you Karate Mom? Do you karate chop everything for dinner? (sorry I couldn’t resist, haha!!) No matter how you chop it up, this looks like a fantastic meal for a busy night.
I’ll be Karate Mom! But I have a feeling my boys are going to be so different that I’ll be Karate Mom, Baseball Mom, Soccer Mom, Boy Scouts Mom!! That’s why they need filling meals like this!
I don’t order chili when going out to eat because it’s always to thick and too much meat for my taste and never looks appetizing. So, I prefer to make it at home. But, I haven’t made it in a long time and you just reminded me. this looks so good and with it on squash… helloooo yumm!!! Now that it’s “cold” again, might have to make it for a nice warm and low carb meal. Thanks Brianne!
What a brilliant idea to serve this deliciousness out of an acorn squash!
This looks delicious! I stocked up and this is one of the sauces I have, I can’t wait to try it!
The chili is so good! It has a great flavor!
Oh my goodness! So much that I enjoy all in one dish. Turkey, chili, acorn squash – YUM!
It turned out to be a fabulous combo! So comforting, but still healthy!
That is so awesome that karate is going so well this far! My niece and nephews both have taken karate for years and it really seems to be amazing for them and their parents too (the discipline, the way they have to address their teacher with “yes sir” etc.)!
I loved that you stuffed the acorn squash full of chili – that’s right up my alley!
He hasn’t quite gotten the “yes sir” down every time, but I think it’s going to be great as he goes along! I love stuffing squash too!
I love stuffed squash. Thanks for a great new recipe!
So many possibilities! You gotta love a natural bowl!!
Hooray to karate mom. This turkey chili acorn looks super cute and McCormick skillet sauce makes dinner appear magically on the table..
It really is fun to watch him! And yes, those McCormick sauces make it so easy!