Combine cherry tomatoes, oil, garlic, salt, and black pepper in a saucepan over medium-low heat. Cook and stir until garlic is just toasted, 2 to 3 minutes.
Pour chicken broth into tomato mixture; bring to a simmer and cook until tomatoes start to collapse and burst, about 10 minutes.
Meanwhile, bring a large pot of lightly salted water to a boil; add penne and cook, stirring occasionally, until tender yet firm to the bite, about 8 to 11 minutes. Drain.
Stir oregano and red pepper flakes into pasta sauce; puree with a stick blender until smooth.
Add penne to tomato sauce; stir until pasta is well coated with sauce. Stir in cheese and season with salt and pepper. Serve and enjoy!
