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Place 4 tortillas on an horizontal surface.
Spread cream cheese on them, leaving a 1-inch (2 cm) border around the tortilla. Sprinkle cheddar cheese on top.
Heat 2 teaspoons olive oil in a skillet and brown chicken pieces. Season to taste. Divide chicken and place on tortillas. Top with cheddar cheese and sprinkle chopped cilantro.
Spread cream cheese on one side of remaining tortillas and place them on top of prepared tortillas, cream cheese down. Press well.
Lightly brush one or two cookie sheets with oil. Place quesadillas on cookie sheets and brush olive oil on top. Bake in oven 350 °F (180 °C) until filling is heated through and edges begin to crisp, about 10 minutes.
With a large spatula, turn quesadillas over, lightly brush olive oil until bottom is crisp, about 5 minutes.
Remove from oven and transfer to plates. Cut in wedges.
Each quesadilla yields 8 wedges.
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