In a large pot of salted boiling water, cook the penne pasta according to package instructions until al dente. Drain and set aside.
In a large skillet, heat 2 tablespoons of olive oil over medium heat. Add the diced chicken breasts, season with salt, pepper, and dried oregano. Cook for about 5-7 minutes or until the chicken is golden brown and cooked through. Remove the chicken from the skillet and set aside.
In the same skillet, add minced garlic and sauté for 1 minute until fragrant. Add the halved cherry tomatoes and cook for about 3-4 minutes until they start to soften.
Stir in the fresh spinach and cook until wilted, about 2 minutes. Then, reduce the heat to low and pour in the heavy cream, stirring to combine.
Add the cooked chicken back to the skillet, along with the cooked pasta and grated parmesan cheese. Toss everything together to ensure the pasta is well-coated in the creamy sauce.
Taste and adjust seasoning with additional salt and pepper if necessary.
Remove from heat and garnish with freshly chopped basil before serving.