In a medium bowl, whisk together Italian salad dressing, balsamic vinegar, honey and red pepper flakes. Set aside.
Heat olive oil in a non-stick 12-inch skillet over medium-high heat. Season chicken with salt and pepper then set chicken evenly in skillet. Cook for 6 minutes, then flip to other side and cook another 6 minutes or until cooked through. Add half of the balsamic mixture to skillet and stir to coat chicken. Remove chicken from skillet and place on a plate. Cover plate with foil to keep warm.
Add asparagus to warm skillet. Season with salt and pepper. Stir and cook for 5 minutes or until crisp-tender. Add chicken back to skillet along with the grape tomato halves. Pour in the rest of the marinade. Gently stir and cook another 5 minutes or until everything is heated through. Serve immediately and enjoy!