Preheat oven to 350°. Line a baking sheet with foil.
Toss butternut squash with 1 Tablespoon oil, maple syrup, honey, cajun seasoning, salt and pepper. Spread evenly on baking sheet. Roast for 25-30 minutes or until squash is tender.
Heat a large Dutch oven over medium-high heat. Add 1 Tablespoon oil. Saute onion, red pepper, jalapeño, and poblano peppers until soft, about 5 minutes. Add chili powder and cumin. Cook for an additional minute.
Add roasted butternut squash, cooked chicken, chipotle, brown sugar, canned tomatoes, chicken stock, corn, and beans. Season with salt and pepper. Reduce heat to low and simmer for 45 minutes. Add more stock if needed.
Ladle into bowls and serve with tortilla chips, sour cream, shredded cheddar cheese, and green onions.