Place halved butternut squash onto a foil lined baking sheet. Drizzle with 2 tablespoons of olive oil and season with salt & pepper. Bake in a 400° oven for 50 minutes.
Take out and when it's cool enough to handle, scoop out the squash and discard the skin.
Heat remaining tablespoon of olive oil and butter in a dutch oven over medium heat. Add onions and cook for 4 minutes. Toss in the garlic and cook for 1 minute. Pour in the squash and stir all the ingredients together. Add in chicken broth and seasonings. Bring to a boil and cook for 5 minutes. Take out bay leaves.
Carefully transfer soup into blender and blend until smooth. Pour soup back into pot and give it a stir. Lastly, add in half & half and stir.
Pour into bowls and add toppings if you have. Enjoy!