In a bowl, combine chicken thighs with olive oil, salt, black pepper, paprika, cumin, cayenne, onion powder, and dried oregano. Mix well to coat.
Heat 1/2 tbsp olive oil in a large skillet over medium heat. Cook the chopped onion and red bell pepper until softened.
In the same skillet, cook the seasoned chicken over medium-high heat until browned and fully cooked through (165°F / 74°C at the thickest part).
Transfer chicken to a cutting board and chop into small pieces.
Assemble: On a tortilla, sprinkle Monterey Jack cheese, then add chopped chicken, sautéed onion and bell pepper, corn kernels, and chopped cilantro. Add a little more cheese, then fold.
Toast folded quesadillas in the skillet over medium heat until golden on both sides and the cheese melts. Slice into wedges and serve.
