Heat a large skillet on medium heat, add 2 tablespoons olive oil, add sliced chicken thighs, season chicken generously with salt, add half of chopped sun-dried tomatoes - and cook everything on medium heat for 5-10 minutes, flipping a couple of times, until the chicken is completely cooked through. Remove the chicken and sun-dried from the skillet, leaving oil in.
Add asparagus (ends trimmed), seasoned generously with salt, remaining half of sun-dried tomatoes, and cook on medium heat for 5-10 minutes until the asparagus cooked through. Remove asparagus to serving plate.
Add chicken back to the skillet, add pesto, stir to coat on low-medium heat until chicken is reheated, 1 or 2 minutes. Remove from heat. Add halved cherry tomatoes, mix with the pesto and the chicken. Add chicken and tomatoes to the serving plate with asparagus.