Preheat your oven to 400°F (200°C) to ensure the quesadilla gets perfectly crispy.
In a large skillet, heat the olive oil over medium heat. Add chopped onion and bell pepper; cook until soft and fragrant, about 5 minutes.
Add chicken pieces along with chili powder, cumin, smoked paprika, garlic powder, salt, and pepper. Stir and cook until chicken is cooked through, about 7-10 minutes.
Mix in black beans and corn; cook for another 2-3 minutes to heat through. Remove from heat and let cool slightly.
On a large sheet pan, lay down four tortillas. Spread half the chicken and vegetable mixture evenly over them. Sprinkle half the shredded Monterey Jack and cheddar cheese on top. Layer remaining tortillas over the filling, pressing down gently.
Top quesadilla with remaining cheese and bake in preheated oven for 15-20 minutes, until tortillas are golden and cheese is melted and bubbly.
Remove from oven and let cool for a couple of minutes. Slice into wedges and serve warm with toppings like salsa, sour cream, or guacamole.