Roughly chop onions and mince garlic. Add to a large pot with 2 Tbsps of butter. Let cook until onions and garlic begin to brown.
2. Add chicken stock, tomatoes, butternut squash (make sure the squash chunks aren't too large, so they won't take forever to cook), salt, pepper, basil, oregano, thyme, brown sugar, cayenne, and chili powder to the pot. Bring to a boil, stirring occasionally. Reduce heat and simmer, uncovered, for 15 minutes. Cover and simmer for an additional 15 minutes. Continue to stir occasionally while soup is simmering.
3. Test butternut squash to see if it's fork-tender. When it is, remove soup from heat, and blend until smooth. I used my NutriBullet, but any blender would do.
4. Return soup to the pot over low heat and stir in cream, milk, and onion powder, Add salt and pepper to taste. Enjoy with a grilled cheese, or by itself!