Line a rimmed baking sheet with aluminum foil and lay out the bacon on it, ensuring the pieces don't overlap. Bake at 375 degrees for 20 minutes, or until crisped. Remove to paper towel-lined plate and break into pieces once cooled. Set aside.
While the bacon is cooking, coat the chicken tenders in Greek seasoning blend. Heat the olive oil in a large cast iron skillet and then add the chicken. Cook until no longer pink in the middle and juices run clear, about 5-7 minutes on each side.
Cut the chicken in chunks and set aside.
Lay out the wraps and spread 1 Tablespoon of Ranch dressing on each.
Sprinkle 2 Tablespoons shredded cheese over half of each of the wraps.
Divide the chicken evenly, spreading over half of each of the wraps.
Sprinkle the sun-dried tomatoes, bacon, and additional 2 Tablespoons shredded cheese over half of each of the wraps, then fold them in half.
Preheat a cast iron skillet to medium and cook the quesadillas one at a time, 3-4 minutes per side, until lightly browned and the cheese has melted.
Remove to plates, cut in half, and serve.