Recipe Background
Layered grilled cheese with slow-cooked beef and tangy accompaniments.
With every bite of this Chicago-Style Grilled Cheese, you’re treated to layers of rich, savory flavors. The tender, slow-cooked beef, reminiscent of a classic Italian beef sandwich, melds beautifully with the sharp provolone. As you take a bite, the tang of pepperoncini cuts through, offering a bright contrast. Giardiniera, if you choose to add it, brings a delightful crunch and a hint of vinegary heat, transforming the simple grilled cheese into something special. Eating it is a sensory journey from the comforting warmth of molten cheese to the explosion of flavors from the beef filling.
In the kitchen, the act of building these sandwiches is an exercise in balance. Start by ensuring your bread is buttered evenly—this simple step guarantees a golden, crispy exterior. The scent of browning butter mingling with the rich beef aroma is just the start. As the sandwich grills, glimpses of melted cheese peeking out the sides signal that something delicious is underway. For the best slices, allow your sandwich to rest briefly after grilling; this helps the layers settle, resulting in cleaner, more satisfying bites.
Share these sandwiches with a group, and you’ll see how food can bring smiles and sparks of conversation. There's something primal yet refined about tearing into a hot, gooey sandwich together. These moments are made for savoring, and this dish is sure to become a regular at gatherings—or just when you're in the mood for something comforting yet full of character.
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
- In a 5 1/2-6-quart slow cooker, add the beef chunks.
- Add the Italian salad dressing mix and the Italian seasoning to the beef.
- 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.
- Add the water to the bottom of the slow cooker.
- 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.
- Transfer the beef chunks to a cutting board.
- Shred the beef chunks.
- Add the beef chunks back to the slow cooker and cover the slow cooker.
- Cook the beef mixture on low until the flavors infuse fully, about 1 hour.
- Preheat a pan over medium heat.
- Using the extra butter, butter 1 side of each slice of the bread.
- Place 1 slice of the buttered bread, buttered-side down, in the hot pan.
- 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.
- 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.
- 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.
- Transfer the sandwich to a plate and repeat the sandwich making and grilling process with the remaining ingredients.
- Serve the sandwiches with the remaining beef cooking liquid for dipping.
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