Slice off the stem of the squash. Starting at the top of the squash, slice the squash lengthwise, to create two long halves. Remove the seeds and gunk.
Brush some olive oil onto the squash and sprinkle with salt and pepper.
Place squash halves cut side down on the baking sheet and roast for 40-50 minutes, depending on how large your squash is. Check on it around 35 minutes of baking time--it's ready when it is tender and easy to scrape the strands with a fork.
While the squash is roasting, prepare the chili.
Remove squash from the oven and use hot pads to flip them over. Fill each with chili. Top with shredded cheese, cilantro and any other yummy toppings. Enjoy!