In a large pot of boiling salted water, cook the penne pasta according to the package instructions until al dente. Drain and set aside.
In a large skillet, heat the olive oil over medium heat. Add the cubed chicken and season with salt, pepper, and red pepper flakes if using. Cook until the chicken is golden brown and cooked through, about 5-7 minutes. Remove the chicken from the skillet and set aside.
In the same skillet, add minced garlic and cook for about 30 seconds until fragrant. Pour in the crushed tomatoes and bring to a simmer.
Stir in the heavy cream, dried oregano, and sugar. Let the sauce simmer for about 5 minutes, allowing it to thicken slightly.
Return the cooked chicken to the skillet, then add the drained penne pasta and grated Parmesan cheese. Toss everything together until well coated in the sauce.
Remove from heat and mix in the fresh basil. Adjust seasoning with additional salt and pepper if needed.
Notes
Serve the pasta in large bowls, garnished with extra Parmesan cheese and fresh basil leaves on top for an appealing finish.