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Preheat the oven to 400F. Line a baking sheet with parchment paper and set aside.
Gently toss the tomatoes with ¼ cup olive oil and layer on the prepared baking sheet in a single layer. Sprinkle with salt and pepper, to taste. Roast for 45 minutes.
In a large dutch-oven, heat olive oil and butter over medium heat. Add the onions, garlic, red pepper flakes, and a pinch of salt. Sauté until onions are translucent and start to brown, about 10 minutes.
Add the canned tomatoes, basil, thyme, roasted tomatoes, including the juices, and chicken stock. Season with salt and pepper, to taste. Bring the soup back to a simmer and cook for 40 minutes, uncovered.
Transfer the soup to a blender and puree until smooth. Taste for salt and pepper. Serve with drizzle of cream or dollop of sour cream, fresh parmesan, and side of grilled cheese.