In a large skillet, heat the 2 teaspoons of olive oil over medium heat. Once hot, add the diced red bell pepper and white onion. Sauté for about 5 minutes, or until the vegetables are soft and the onions are translucent. Stir in the minced garlic and cook for an additional minute until fragrant.
In a mixing bowl, combine the sautéed vegetables, sliced black olives, roasted corn, shredded chicken, minced chipotle pepper, and half of the Monterey jack cheese. Mix everything thoroughly until well combined.
Lay out four flour tortillas on a clean surface. Evenly distribute the chicken and vegetable mixture onto each tortilla, then sprinkle the remaining cheese on top before placing another tortilla over each filled tortilla.
Return the skillet to medium heat. Carefully place one quesadilla in the skillet and cook for about 3-4 minutes on each side, or until golden brown and crispy. Repeat with the remaining quesadillas, adding more olive oil to the skillet if necessary.
Once cooked, remove the quesadillas from the skillet and let them cool for a minute. Cut each quesadilla into wedges and garnish with fresh cilantro. Serve with your favorite salsa or guacamole for dipping!