Cut the chicken breast into thin, bite-sized pieces for even cooking. Combine cumin, garlic powder, salt, and black pepper in a small bowl, then sprinkle the seasoning blend over the chicken pieces until fully coated with the aromatic spice mixture.
Heat olive oil in a large skillet over medium-high heat until it shimmers slightly. Once ready, add the seasoned chicken and cook for 6–8 minutes, stirring occasionally, until the internal temperature reaches 165°F and the exterior develops a light golden color.
Add diced bell peppers and onion to the cooked chicken, stirring gently to combine. Let the mixture cook for an additional 3–4 minutes until the vegetables soften and release their natural sweetness into this cozy after school quesadilla dinner filling.
Reduce heat to medium and remove the chicken mixture to a clean plate, setting aside for assembly. Wipe out the skillet with a paper towel, then melt 1 tbsp butter over medium heat for toasting each tortilla.
Place the first tortilla in the butter and toast for 1–2 minutes on each side until it becomes pliable and golden. Spread half the shredded cheddar cheese on one half of the toasted tortilla, then layer the chicken and vegetable mixture generously.
Top with the remaining cheese, sliced jalapeño, and cilantro before folding the tortilla in half. This soft, cheesy quesadilla should hold together beautifully with the warm cheese acting as the ideal binding agent.
Place the folded quesadilla back in the buttered skillet and cook for 2–3 minutes per side until both sides develop a crispy golden exterior while the cheese inside melts completely. Repeat with the second tortilla and remaining filling.
Transfer quesadillas to a cutting board and let rest for 2 minutes before slicing into triangles. Serve immediately with sour cream and salsa on the side for dipping and customization.