Preheat Over to 400F. Spray a cooking sheet or put foil down on the pan.
Place squash halves on the baking sheet, cut sides down. Make sure all the seeds have been removed. Bake until soft, about 30 minutes.
Meanwhile, in a large skillet, brown turkey over medium heat, breaking it up as it cooks into smaller pieces and season with salt and pepper.
When meat is cooked, strain and place back in pan. Add in onion and garlic, cook 3 minutes over medium heat. Next, add the can of rotel tomatoes, tomato sauce, water, cumin, chili powder, paprika and bay leaf.
Cover and simmer over medium-low heat about 25 minutes stirring occasionally, until sauce reduces and thickens slightly.
Remove bay leaf, flip the squash over and fill each half with 3/4 cup of chili. Top with some cilantro and enjoy!