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Skillet Steak and Veggies with Chimichurri

Marinated flank steak seared in a cast iron skillet, then tomatoes, asparagus, and onions cooked in the same pan and finished with fresh homemade chimichurri. A steakhouse dinner for two, made at home.
Prep Time 20 minutes
Cook Time 25 minutes
Marinate and Rest 2 hours
Serving Size 2 people

Ingredients

For the Marinade

  • 1 tablespoon salt
  • 1 teaspoon black pepper
  • 1/2 cup extra virgin olive oil
  • 3 tablespoons balsamic vinegar
  • 2 teaspoons Worcestershire sauce
  • 1 heaping teaspoon minced garlic
  • 1 flank steak cut in half

For the Chimichurri Sauce

  • 1/2 cup fresh Italian parsley chopped
  • 2 tablespoons fresh oregano chopped
  • 1 teaspoon crushed red pepper
  • 2 tablespoons red wine vinegar
  • 1 tablespoon minced garlic
  • 1/2 cup olive oil
  • Salt and pepper to taste

For the Skillet

  • 3 tablespoons olive oil divided
  • 1/3 large red onion thinly sliced
  • 4 green onions sliced
  • 1/2 bunch asparagus woody ends snapped off
  • 2 cups grape or cherry tomatoes halved lengthwise

Instructions

Marinate the Steak

  • Add the salt and pepper to a gallon zip-top bag, then add the olive oil, balsamic vinegar, Worcestershire sauce, and minced garlic. Roll the top of the bag back so it stands upright while you pour.
  • Gently shake the bag to combine the marinade.
  • Add the flank steak halves, press out most of the air, seal the bag, and move the steak around so the marinade coats it all over.
  • Refrigerate 30 minutes to 4 hours. Two hours is ideal.

Make the Chimichurri

  • Pull the leaves from the parsley stems, gather them into a bundle, and give them a rough chop until you have about 1/2 cup.
  • Strip the oregano leaves by pinching the stem and sliding backward, then chop until you have about 2 tablespoons.
  • In a bowl, combine the chopped parsley, chopped oregano, crushed red pepper, red wine vinegar, minced garlic, and olive oil. Season with salt and pepper to taste and stir well.
  • Set aside at room temperature while you cook so the flavors have time to meld.

Prep and Cook

  • Heat a cast iron skillet over medium to medium-high heat and add 2 tablespoons of olive oil.
  • Thinly slice the red onion, slice the green onions all the way into the white parts, and reserve a small amount of green onion for garnish.
  • Snap the woody ends off the asparagus by bending each spear until it breaks naturally.
  • Place the marinated steak directly into the hot skillet and cook 4 minutes per side for medium rare. Add 1 to 2 extra minutes per side for more doneness.
  • While the steak cooks, slice the tomatoes in half lengthwise.
  • Remove the steak from the skillet and let it rest for 10 minutes.
  • Add the remaining 1 tablespoon of olive oil to the skillet, then the red onion and green onion. Cook 3 to 4 minutes until softened.
  • Add the asparagus and cook about 5 minutes until tender.
  • Add the tomatoes for the final 40 seconds, just until they begin to burst.

Bring It Together

  • Turn off the heat. Return the rested steak to the skillet on top of the vegetables and pour in any collected juices.
  • Drizzle about half the chimichurri over the steak and vegetables, reserving the rest to serve at the table.
  • Let the skillet sit off the heat a couple of minutes, then plate and sprinkle with the reserved green onions.

Video

Notes

  • Flank steak takes a marinade beautifully, but sirloin, flat iron, or skirt steak all work well here.
  • Don't marinate longer than 4 hours — the acid in the vinegar will start to change the texture of the meat.
  • For temperature accuracy, pull the steak at 130°F for medium rare or 140°F for medium.
  • The chimichurri can be made up to a day ahead. Keep it covered in the refrigerator and bring it to room temperature before serving.
  • To double this for four, use a whole flank steak and sear it in two batches so the pan doesn't get crowded.
  • The crushed red pepper gives warmth rather than heat. Cut it to 1/2 teaspoon or leave it out if you're sensitive to spice.