Grilled Steak-and-Onion Quesadillas

Quesadillas are an easy way to make a quick, no-fuss but very tasty casual dinner—or party food, if you cut them into smaller pieces. Fillings are very versatile but keep in mind that overstuffing can prevent the tortillas from holding together when grilled, so don’t add too many ingredients to each one.

I normally prepare the filling ingredients in the same pan as I grill the quesadillas, but this time I took the onion slices and steak outside to grill over charcoal. However, I still grilled the filled quesadillas in a grill pan inside. You can use a grill pan (or cast-iron skillet) start to finish for this recipe, if you choose to keep it all inside.

Note: If you can’t find a small enough flank steak, choose a thick, boneless New York strip or rib-eye instead.  

Flank Steak

Makes 2 quesadillas

Ingredients

• 1 large yellow onion, cut into 1/2-inch-thick rounds
• 3/4-lb flank steak, about 1-inch thick
• olive oil for brushing, plus 1 tbsp
• sea salt
• freshly ground black pepper
• 2 cayenne chiles, finely chopped
• 1 garlic clove, finely chopped
• 2 large stem tomatoes, chopped (about 1-1/2 cups)
• 1/2 tsp dried oregano
• 4 8-inch-diameter flour tortillas
• 1 cup shredded Monterrey jack and cheddar cheese mixture
• salsa and sour cream, for serving (optional)

Preparation

1. Heat a grill pan (or light a grill) for medium-high heat.
2. Brush both sides of the onion slices and steak with oil and season with salt and pepper.
3. Grill the onion slices until charred and crisp-tender, about 3 minutes per side. Transfer to a cutting board.
4. Grill the steak until charred outside and pink in the middle, about 5 minutes per side (or until desired degree of doneness). Transfer to a cutting board. (Wipe out excess oil and any steak or onion particles from the grill pan, if using.)

Grilled Onion

Flank Steak Beginning to Grill

Grilled Steak

1. Meanwhile, heat a skillet or saucepan over medium heat and add 1 tablespoon of olive oil. Add the cayenne chiles and garlic and sauté 3 minutes.
2. Add the tomatoes and oregano and season with salt and pepper. Cook until the tomatoes break down to form a saucy consistency, 6-7 minutes. Remove from the heat and let cool 5 minutes.

Chile and Garlic 

Tomato Mixture Beginning to Cook 

Cooked Sauce

1. Lay the tortillas on a work surface and divide the chile-tomato mixture over two, spreading almost to the edges.
2. Thinly slice the steak across the grain and divide on top of the chile-tomato mixture. Coarsely chop the onion slices and divide on top of the steak.
3. Divide the cheese and scatter over both. Place the remaining tortillas on top and press gently.

Sauce Layer

Thinly Slice the Steak

Chopped Onion 

Steak Layer

Onion Layer 

Cheese Layer

1. Re-heat the grill pan over medium-high heat and brush with olive oil. Lay 1 quesadilla in the pan and press with a grill press or large spatula. Continue pressing until the bottom tortilla begins to crisp and has grill marks, about 3 minutes.
2. Turn and grill until the other side has grill marks and the quesadilla is hot throughout, about 2 minutes longer. Transfer to a cutting board and repeat with the other quesadilla.

Quesadilla Beginning to Grill 

Quesadilla after Turning

Grilled Quesadilla 

Slice each quesadilla into wedges and serve salsa and sour cream dolloped on top or alongside, if desired.

Grilled Steak-and-Onion Quesadillas