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Preheat oven to 350°F. Spread tortilla strips in an even layer on two large baking sheets. Bake for 15 minutes. Cool on a wire rack.
Heat oil in an extra-large skillet over medium-high heat. Add onion, garlic and oregano; cook for about 3 minutes or until onion is softened, stirring occasionally. Add tomatoes, chipotles and the reserved 1 teaspoon adobo sauce. Bring to a boil; cook for 1 minute, stirring occasionally. Add broth; return to a boil. Simmer, uncovered, for 5 minutes. Add chicken and black pepper; heat through.
Set aside a few baked tortilla strips. Gradually stir the remaining tortilla strips into the chicken mixture; heat through. Remove from heat; sprinkle with cheese. Garnish with cilantro sprigs and the reserved tortilla strips. In a small bowl, combine sour cream and milk; serve with the chilaquiles.