On a work surface, spread 2 of the tortillas. Sprinkle the cheddar cheese over the bottom of each tortilla.
Add the apples evenly on top of the cheese, sprinkle with cinnamon, then top with bacon. Top with another tortilla.
Heat a large nonstick skillet with cooking spray over medium heat.
Carefully place 1 quesadilla in pan and cook 2 minutes. Using a spatula, gently flip the quesadilla and cook an additional 2 minutes until lightly browned and cheese is melted.
Repeat with second quesadilla. Serve warm and drizzle with maple syrup.