Heat oil in a large pot over medium-high heat. Add onion and cook until softened, about 3-4 minutes. Add garlic, oregano, chili flakes, salt and pepper, and continue cooking until flavors combine and garlic begins to cook, about 2-3 more minutes. Deglaze the pan with white wine and reduce by about half. Add in cherry tomatoes, stir and cover the pan. Cook the tomatoes until they just begin to burst, about 4-5 minutes.
Remove the lid and carefully mash the tomatoes with a wooden spoon or potato masher. Add chicken stock to the pan then nestle the linguine in the stock. Cover the pan again and cook for 10 minutes.
Remove the lid, give the pasta stir and resume cooking for another 5 minutes, or until pasta is cooked through to al dente. Add in arugula and stir to combine.
Serve in shallow bowls garnished with Parm.
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