Heat the olive oil in a large saucepan over medium heat. Add the onion and cook until soft and translucent, 5 to 6 minutes. Add the garlic and continue cooking, stirring continually, until fragrant and barely golden, 2 minutes additional.
Add the tomatoes, chicken broth, oregano and crushed red pepper. Stir to combine and season to taste with salt and pepper. Reduce the heat to medium low, add the basil, cover and cook for 20 minutes, stirring occasionally.
Stir in the cream and purée the soup using a hand-held or conventional blender. Ladle into bowls and garnish with chopped basil if desired.