Boil the penne pasta in salted water according to package instructions until tender. Drain and rinse with cold water to cool.
Grill or pan-sear the chicken breast until cooked through and juices run clear. Let cool, then dice into bite-sized pieces.
In a large mixing bowl, combine the cooked pasta, diced chicken, cherry tomatoes, cucumber, red bell pepper, red onion, black olives, and chopped basil.
Pour the Italian vinaigrette dressing over the salad and toss gently to combine all ingredients evenly.
Serve the salad in a clear, portable airtight container. Include a small separate container with extra dressing for added flavor at serving.