Cook pasta according to package directions. Drain and let cool.
Massage chopped kale with a splash of olive oil or a bit of the dressing until softened—about 1–2 minutes.
In a large bowl, combine the pasta, chicken, kale, and cherry tomatoes.
Add Caesar dressing and toss to coat everything evenly.
Sprinkle Parmesan cheese over the top, add salt and pepper to taste.
If using, top with croutons just before serving for crunch.