In a large skillet, heat 2 tablespoons of olive oil over medium heat. Season the boneless skinless chicken thighs with salt, then add them to the skillet along with 1/4 cup of sun-dried tomatoes. Cook for 5-10 minutes, turning occasionally, until the chicken is golden brown and reaches an internal temperature of 165°F. Remove from skillet and set aside.

With the skillet still over medium heat, add 1 bunch of chopped asparagus and another 1/4 cup of sun-dried tomatoes to the leftover oil. Sauté for about 5-10 minutes until the asparagus is bright green and tender-crisp.

While the asparagus cooks, bring a large pot of salted water to a boil. Add tortellini and cook according to package instructions, about 3-5 minutes. Drain and set aside, reserving a bit of pasta water.

Return the chicken and sun-dried tomatoes to the skillet with asparagus. Add 1/2 cup of basil pesto, stirring well to coat everything. Cook for an additional 1-2 minutes to heat through.

Gently fold in the cooked tortellini and 1 cup of halved cherry tomatoes, stirring until well combined. If the mixture is dry, add a splash of reserved pasta water. Serve immediately.