Heat olive oil in a large heavy-bottomed pot over medium-high heat.
Add the diced onion and bell pepper, sautéing for 5 minutes until the vegetables are softened.
Add the ground turkey to the pot, cooking and breaking it into crumbles until fully browned.
Stir in the minced garlic, chili powder, cumin, oregano, and smoked paprika, cooking for 1 minute until fragrant.
Incorporate the cubed butternut squash, crushed tomatoes, black beans, and chicken broth; stir to combine.
Bring the mixture to a gentle boil, then reduce the heat to low.
Simmer covered for 30 minutes, then remove the lid and simmer for an additional 15 minutes until the squash is fork-tender and the chili has thickened.
Season with salt and black pepper to taste before serving.