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Preheat your oven to 400°F (200°C). Bring a large pot of salted water to a boil and cook pasta to al dente. Reserve 1 cup of the pasta water, drain the rest, and set aside.
Arrange the broccoli florets on a lined baking sheet, drizzle with 1 tablespoon of olive oil, and season with salt and pepper. Roast in the oven for 15-18 minutes.
In a large sauté pan, cook the bacon over medium-high heat until browned and crispy. Remove and set on a paper towel-lined plate.
Without wiping the pan, add the onions and cook until tender, about 3 minutes. Add the garlic and cook for 1 more minute. Season with oregano.
Add the chicken stock, scraping up any browned bits from the pan, and let the liquid reduce for 4-5 minutes.
Add the cooked pasta, roasted broccoli, and bacon to the pan. Toss to coat. If needed, add reserved pasta water to loosen the sauce.
Season with red chili flakes, drizzle with the remaining olive oil, and toss.
Serve with freshly grated Parmesan cheese and enjoy!