Preheat the oven to 400 degrees F.
Place the butternut squash on a large baking sheet. Drizzle with 1 tablespoon of the olive oil, then add the chili powder, salt, and pepper. Toss everything together to evenly coat.
Bake the squash at 400 degrees F for about 20 minutes, stirring halfway through, until squash is soft and cooked through. When done, set squash aside for now and leave oven on.
Meanwhile, about 10 minutes before the squash will be done, heat the remaining 1 tablespoon of olive oil in a skillet over medium-low heat. Add the cranberries and cook for 5 minutes.
Add the brown sugar and spinach to the pan and cook for another minute, until cranberries are soft and spinach is starting to wilt.
Spread the tortilla chips onto a baking sheet. Top with the butternut squash and cranberry/spinach mixture. Add the cheddar cheese on top of that.
Bake the nachos in the oven at 400 degrees F for 7 to 9 minutes, until the cheese is melted. Dig in and enjoy!