Preheat oven to 375 degrees F and line 2 large baking sheets with parchment paper or silicone mats.
In a large mixing bowl, add chicken, bell peppers, cumin, salt and pepper. Stir well to combine.
Build each quesadilla: On a half of tortilla sprinkle 1 1/2 tbsp cheese, spread heaping 1/2 cup filling and sprinkle with 1 1/2 tbsp of cheese. Fold the other half of tortilla on top pressing on it somewhat gently-hard making a half moon shape. Place on a baking sheet.
Repeat and make 11 more quesadillas, arranging 3-4 quesadillas on a baking sheet. If you have any leftover filling – eat it.
Bake for 25 minutes. Remove from the oven, let rest for 1-2 minutes and cut each quesadilla in half using serrated or sharp knife.
Make Ahead: Refrigerate filling mixture covered for up to 2 days, then make quesadillas.
Freeze: For each quesadilla, assemble and then wrap in plastic wrap as tightly as possible without compromising its shape. Lay flat in a gallon size Ziploc bag, squeeze as much air out as possible, seal and freeze for up to 3 months. When ready to enjoy, bake from frozen at 375 degrees F for 25-30 minutes. Or alternatively cook in a panini press.