Lay two tortilla downs, and top each with 1/2 cup of the cheese.
Top with the cheese on each tortilla with 1/2 cup chicken and 2 slices crumbled bacon each.
Spread 2 tablespoons of ranch dressing on the remaining 2 tortillas and put ranch side down on top of the bacon.
Heat 1 tbsp of olive oil over medium high heat in large skillet. Place one of the quesadillas cheese side down over hot oil.
Cook 4-5 minutes, then carefully flip over. Cook another 3-4 minutes.
Repeat with remaining quesadilla.
Cut into triangle slices.