Step 1

Add olive oil, adobo sauce, minced chipotle pepper, lime juice, apple cider vinegar, garlic, oregano, cumin, paprika, salt, and pepper to a medium bowl. Whisk to combine.

Step 2

Place the steak in a resealable bag or shallow dish. Pour the marinade over it, ensuring the steak is fully coated. Cover and refrigerate it for at least 1 hour.

Step 3

Add the red wine vinegar, honey, adobo sauce, oregano, cumin, salt, and black pepper to a small bowl. Whisk to combine. Slowly drizzle in olive oil while whisking until well combined. Set aside or refrigerate until ready to serve.

Step 4

Heat a cast-iron skillet or grill pan over medium-high heat. Remove the steak from the marinade, letting excess drip off. Cook 3–4 minutes per side for medium-rare or longer for desired doneness.

Step 5

Transfer the steak to a cutting board. Let it rest for 5 minutes before slicing it against the grain into thin strips.

Step 6

Heat a large skillet or griddle over medium heat. Place a tortilla in the skillet and sprinkle 1/2 cup of Monterey Jack cheese evenly over one half. Add the sliced steak and fajita veggies. Sprinkle it with 1/4 cup white cheddar cheese and fold the tortilla in half.

Step 7

Cook for 2–3 minutes per side, pressing gently with a spatula, until golden brown and the cheese is melted. Remove from heat and repeat with the remaining tortillas and fillings.

Step 8

Slice each quesadilla into triangles and serve with the honey chipotle vinaigrette on the side for dipping. Enjoy your Chipotle-style steak quesadillas fresh and hot!