Set a large skillet or pot over medium-high heat. When it’s hot, add the ground beef, diced yellow onion, diced red and orange bell peppers, and crumble the beef with a wooden spoon as it cooks. Add the minced garlic and, if using, the minced habanero pepper for a spicy kick. Continue cooking until the beef is fully browned and the vegetables have softened, about 7-8 minutes. Drain any excess fat from the pan before proceeding.
Transfer the browned beef and sautéed vegetables to a slow cooker or keep them in the pot if using the stovetop method. Add the pumpkin puree, tomato sauce, drained pinto beans, water, chili powder, pumpkin pie spice, and salt. Stir everything together until well combined. If using a slow cooker, cover and cook on HIGH for 4 hours or LOW for 8 hours. For stovetop, bring to a boil, then lower the heat to a simmer.
If cooking on the stovetop, let the chili simmer for about 30 minutes, stirring occasionally to prevent burning. If using a slow cooker, let the ingredients cook for the designated time. This allows the flavors to meld fully and the chili to thicken. I like to give the chili a stir every so often to ensure nothing sticks to the bottom of the pot.
Stir your finished chili and ladle it into bowls. Top with shredded cheddar cheese and sliced green onions according to your preference. Serve with a side of your favorite cornbread—pumpkin or classic both work great. For a flavor boost, I sometimes add a squeeze of lime or a dollop of sour cream to each bowl as well.