In a large pot, bring salted water to a boil. Add the penne pasta and cook according to package instructions until al dente. Drain and set aside, reserving a little pasta water.
In a large skillet, heat the olive oil over medium heat. Add the sliced chicken breast to the skillet, season with salt and pepper, and cook until golden brown and cooked through (about 5-7 minutes). Remove the chicken from the skillet and set aside.
In the same skillet, reduce the heat to low. Pour in the heavy cream and stir in the basil pesto, mixing well until combined and warmed through.
Add the cooked penne pasta to the skillet along with the sautéed chicken and halved cherry tomatoes. Toss everything together, adding reserved pasta water if needed to create a creamier consistency.
Stir in the grated Parmesan cheese until melted and creamy. Taste and adjust seasoning with additional salt and pepper if needed.
Plate the dish and garnish with fresh basil leaves for a delightful aroma and presentation.