Save There's something magical about the moment when comfort food gets a personality upgrade. I was cleaning out my pantry one chilly evening, staring down a box of elbow macaroni and a jar of hot honey I'd impulse-bought weeks earlier, when it hit me—why not build an entire meal around that sweet-spicy contrast? The acorn squash halves were already there, waiting for something more interesting than the usual roasted vegetable side. That night, I created this dish almost by accident, and it's become the kind of recipe I keep coming back to when I need something that feels both cozy and a little bit adventurous.
I made this for my sister's surprise dinner party last fall, and watching everyone's faces light up when they saw those golden squash halves stuffed with creamy, bubbling chili mac was worth every minute of prep work. One guest asked if I'd been taking cooking classes—I just smiled and didn't mention the pantry clean-out origin story. She went home asking for the recipe, and now it's apparently a regular in her kitchen too.
Ingredients
- Acorn squash: Medium-sized ones are the sweet spot, holding just enough chili mac without becoming unwieldy to eat.
- Olive oil: Use a decent quality for the roasting, as it'll caramelize the squash beautifully.
- Yellow onion: Diced small so it softens into the background and adds sweetness to the filling.
- Garlic: Two cloves minced fine will give you flavor without overpowering the spice blend.
- Red bell pepper: Adds color and a subtle sweetness that plays nicely with the hot honey.
- Jalapeño: Seed it if you want gentle heat, or leave seeds in if you're feeling bold.
- Kidney and black beans: Both canned and rinsed—they add protein, texture, and earthiness to the filling.
- Diced tomatoes: Canned works perfectly here and saves you precious time.
- Vegetable broth: Keeps the pasta from drying out as it cooks in the skillet.
- Chili powder, cumin, and smoked paprika: This trio is your flavor foundation, so don't skip any of them.
- Hot honey: The star player—it balances heat with sweetness in a way that feels unexpected and right.
- Elbow macaroni: Cooks directly in the skillet with the chili, absorbing all those flavors as it softens.
- Sharp cheddar cheese: The sharpness cuts through the richness and won't disappear into the dish.
- Fresh cilantro: A bright, herbaceous finish that makes the whole plate feel intentional.
Instructions
- Prepare and roast the squash:
- Preheat your oven to 400°F and line a baking sheet with parchment paper. Brush the cut sides of your squash halves generously with olive oil, then season with salt and pepper—don't be shy, as this is what gives you those caramelized, nutty edges. Place them cut-side down on the sheet and roast for 35 to 40 minutes until a fork pierces the flesh with almost no resistance.
- Build your flavor base:
- While the squash works its magic in the oven, heat olive oil in a large skillet over medium heat. Add your diced onion and let it cook undisturbed for about 3 minutes until it softens and becomes translucent. Stir in the garlic, red bell pepper, and jalapeño, then cook for another 4 to 5 minutes, stirring occasionally, until everything smells incredible and the peppers have started to soften.
- Combine beans, tomatoes, and spices:
- Pour in both cans of beans (drained and rinsed), the diced tomatoes with their juice, and your vegetable broth. Add the chili powder, cumin, smoked paprika, salt, and pepper, then stir everything together and bring it to a gentle simmer. Let it bubble away for a few minutes so the spices can bloom and mellow into the sauce.
- Cook pasta right in the skillet:
- Stir in your dry elbow macaroni and the hot honey, mixing well so the pasta is submerged. Cover the skillet and let it cook for 8 to 10 minutes, stirring occasionally, until the pasta is tender but still has a little bite. If it starts looking too thick and dry, add a splash more broth or water.
- Finish with cheese:
- Remove the skillet from heat and stir in your shredded sharp cheddar cheese until it's completely melted and the whole mixture becomes creamy and cohesive. Taste it and adjust salt or heat to your preference.
- Assemble and serve:
- Once your roasted squash halves are cool enough to handle, flip them cut-side up on a serving plate or directly on plates. Spoon generous portions of the chili mac into each half, letting it mound slightly. Drizzle with extra hot honey and scatter fresh cilantro over the top before serving.
Save The real magic happened when my neighbor smelled this cooking and stopped by right as I was plating it. She took one bite and immediately wanted to know everything, then came back three days later with tomatoes from her garden, ready to make her own version. That's when I realized this dish had crossed from just-dinner into something that sparks conversation and brings people together.
The Hot Honey Secret
Hot honey seems like a trendy ingredient, but it's genuinely transformative in this recipe. The heat doesn't announce itself loudly; instead, it sneaks up on you after the creaminess and cheese have done their work, creating this gorgeous three-act flavor experience. I learned that the best hot honey is the one you actually have on hand, so if you're making your own by stirring hot sauce into regular honey, use whatever level of heat you enjoy—there's no single right answer.
Customizing Your Filling
This recipe is a framework, not a rulebook. Some nights I add crumbled cooked ground turkey for extra protein, and it slots right in without changing the balance. Other times I swap the black beans for pinto beans, or use pepper jack cheese instead of cheddar for something tangier and spicier. The dish remains itself while becoming whatever you need it to be.
Make It Your Own
The beauty of this dish lies in how forgiving it is of substitutions and adjustments. You could add corn, diced zucchini, or mushrooms to the filling without losing the essence of what makes it special. Some people swear by a pinch of cocoa powder stirred into the chili, which adds an almost invisible depth that keeps people guessing at what makes it taste so good.
- For dairy-free versions, plant-based sharp cheddar actually melts beautifully and doesn't compromise the creamy texture.
- Gluten-free pasta works perfectly here since it's cooking in liquid anyway, making it less prone to mushiness than if you were boiling it separately.
- This dish keeps beautifully in the refrigerator for 3 days and reheats wonderfully in a low oven, making it perfect for meal prep or feeding a crowd.
Save This dish has become my go-to when I want something that feels special without requiring hours in the kitchen. Every time I make it, it reminds me that the best meals are the ones where a little creativity meets what you already have on hand.
Kitchen Help
- → Can I make this dish ahead of time?
Yes, you can roast the squash and prepare the chili mac up to 2 days in advance. Store them separately in the refrigerator. When ready to serve, reheat both components, stuff the squash, and add the final garnishes.
- → What type of squash works best?
Acorn squash is ideal because its naturally sweet flavor pairs beautifully with the spicy chili mac, and its shape creates a perfect bowl. Delicata or butternut squash also work well if acorn isn't available.
- → How can I adjust the spice level?
Control the heat by varying the amount of jalapeño and choosing mild or spicy hot honey. For extra kick, add cayenne pepper or use pepper jack cheese instead of cheddar. Reduce or omit the jalapeño for a milder version.
- → Can I freeze these stuffed squash?
You can freeze the assembled stuffed squash before baking for up to 3 months. Wrap each half tightly in plastic and foil. Thaw overnight in the refrigerator, then reheat at 375°F until warmed through, about 20-25 minutes.
- → What can I serve alongside this dish?
The stuffed squash is quite filling on its own, but a simple green salad with tangy vinaigrette balances the richness. Crusty bread for soaking up extra sauce, or roasted vegetables like Brussels sprouts make excellent sides.