In the same skillet, add the remaining 1 tablespoon of olive oil. Add the asparagus pieces and cook for 3-4 minutes until they begin to soften.
Add the halved cherry tomatoes and the cheese tortellini to the skillet with the asparagus. Stir in 1/4 cup of water, cover tightly with a lid, and let steam for 3-4 minutes until the tortellini is tender.
Return the cooked chicken to the skillet. Turn off the heat completely.
Stir in the basil pesto, tossing well to coat the chicken, vegetables, and pasta evenly. Garnish with fresh basil leaves and serve immediately.