Preheat oven to 400. Drizzle the oil on a large sheet pan. Put the chicken breasts and aspargus on the pan. Put the bacon and sundried tomatoes on top. Sprinkle with the salt and pepper.
Bake for 25 minutes or until chicken is cooked through and reads 160 on a meat thermometer. Stack asparagus on top of the chicken, put a slice of cheese on top, sprinkle with tomatoes and bacon, and bake for an additional 3-4 minutes to melt the cheese.