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Test Kitchen Approved

Chicago-Style Grilled Cheese

Time: 9 hours 20 minutes

Yield: 10 servings

About

Chicago-Style Grilled Cheese is out of this world, the kind of sandwich that doesn't just impress but pays homage to the various culinary influences in the Windy City. The melty provolone cheese and buttery, golden bread slices envelop extra-tender, savory beef, spicy pepperoncini, and sour giardiniera. There's richness, succulence, tartness, and plenty of balance! Chicago-Style Grilled Cheese is a Chi-City marvel!

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Ingredients

  • 1 (3-pound) chuck roast, trimmed of visible fat, cut into large chunks
  • 1 (0.7-ounce) envelope dry Italian salad dressing mix
  • 1 1/2 teaspoons Italian seasoning
  • 1/2 medium onion, chopped
  • 2 beef bouillon cubes
  • 2 tablespoons unsalted butter, plus more, to taste
  • 1 (8-ounce) jar pepperoncini pepper slices, juices reserved, plus more, to taste
  • 2 cups water
  • 1 (20-ounce) loaf artisan bread, sliced
  • provolone cheese, to taste, sliced
  • Chicago-style Italian sandwich giardiniera, optional, to taste, store-bought or homemade

Directions

Step 1 -In a 5 1/2-6-quart slow cooker, add the beef chunks.

Step 2 -Add the Italian salad dressing mix and the Italian seasoning to the beef.

Step 3 -Add the onions, the bouillon cubes, 2 tablespoons of the butter, and 1 jar of the pepperoncini slices to the bottom of the slow cooker.

Step 4 -Add the water to the bottom of the slow cooker.

Step 5 -Cover the slow cooker and cook until the beef chunks are cooked through to an internal temperature of 160 degrees F and shreds easily with a fork, about 8 hours.

Step 6 -Transfer the beef chunks to a cutting board.

Step 7 -Shred the beef chunks.

Step 8 -Add the beef chunks back to the slow cooker and cover the slow cooker.

Step 9 -Cook the beef mixture on low until the flavors infuse fully, about 1 hour.

Step 10 -Preheat a pan over medium heat.

Step 11 -Using the extra butter, butter 1 side of each slice of the bread.

Step 12 -Place 1 slice of the buttered bread, buttered-side down, in the hot pan.

Step 13 -Immediately top the bread slice evenly with the provolone, the beef mixture, the extra pepperoncini slices, and the giardiniera. Make sure you drain each individual portion of the beef mixture before adding it on top of the bread slices.

Step 14 -Add 1 slice of the provolone on top of the giardiniera layer, then close the sandwich with 1 slice of the bread, buttered-side up.

Step 15 -Grill, flipping the sandwich once, until the cheese is melted and the bread is golden-brown on both sides, about 2-4 minutes per side.

Step 16 -Transfer the sandwich to a plate and repeat the sandwich making and grilling process with the remaining ingredients.

Step 17 -Serve the sandwiches with the remaining beef cooking liquid for dipping.

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