Chicago Italian Beef Recipe

Prepare and Sear Beef

Pat the chuck roast dry with paper towels and trim excess large fat if desired. Season all over with 1 tsp salt and 1 tsp freshly ground black pepper. Heat a large Dutch oven or heavy-bottomed pot over medium-high heat and add 2 tbsp olive oil. When oil is hot and shimmering, sear the roast 4–5 minutes per side until deeply browned. Remove the roast to a plate.

Sauté Aromatics

Lower heat to medium. Add the halved and sliced onion to the pot and sauté 4–5 minutes until softened and beginning to brown, scraping up browned bits. Add the 6 smashed garlic cloves and sauté 30–45 seconds until fragrant.

Deglaze and Build Braising Liquid

Pour in 1 cup dry red wine to deglaze, using a wooden spoon to loosen browned bits from the bottom. Let wine simmer 2–3 minutes to reduce slightly. Add 4 cups beef stock, 1 tbsp Worcestershire sauce, 2 tsp dried oregano, 1 tsp dried basil, 1 tsp dried thyme, 1 tsp crushed red pepper flakes, 2 bay leaves and 1.5 tsp salt. Stir to combine.

Braise the Beef

Return the seared roast to the pot so at least half is submerged in liquid. Bring to a gentle simmer, then cover and transfer to a 325°F (160°C) oven. Braise until the beef is very tender and easily pulls apart, about 3 to 3.5 hours (check after 2.5 hours). Alternatively, simmer gently on the stovetop over low heat for the same time.

Rest and Shred

Remove the roast and place on a cutting board. Strain and reserve the braising liquid into a fat separator or large measuring cup; discard bay leaves and any large solids. Let the roast rest 10 minutes, then use two forks (or meat claws) to shred the beef into bite-sized strips. Taste the reserved jus and adjust seasoning with additional salt if needed.

While the beef braises in the last 45 minutes, heat a skillet over medium heat and add a small splash (about 1 tbsp) of the reserved braising liquid or 1 tsp olive oil. Add the sliced green bell pepper and sauté until softened, about 6–8 minutes. Stir in the 1/2 cup sliced banana peppers just to warm through for 1–2 minutes. Transfer peppers to a bowl and keep warm. (If you prefer all peppers cooked into the beef, add them to the braising pot for the final 30 minutes.)

Combine shredded beef with some au jus: place shredded beef in a wide shallow pan or back in the Dutch oven and pour enough reserved au jus over it to moisten (start with 1 to 1 1/2 cups). Warm over low heat until the beef absorbs some liquid and is hot, 8–10 minutes. Taste and add more jus for a wetter sandwich (dip) or less for a drier filling.

Prepare rolls: Preheat broiler or toaster oven. If toasting, lightly butter the cut sides of each roll (optional). Place rolls cut-side up under the broiler for 1–2 minutes until edges are lightly browned — watch carefully to prevent burning.

Assemble sandwiches: Pile a generous portion of the shredded, juiced beef onto the bottom half of each roll. Top with sautéed green peppers and a spoonful of chopped giardiniera. If you want a cheesy Italian beef, place a slice of provolone over the hot beef and briefly broil or cover with a lid for 30–60 seconds to melt.

Serve with au jus for dipping: Pour reserved warm au jus into small bowls or ramekins at the table so diners can dip (wet) their sandwiches to preference. Serve extra giardiniera and pickled banana peppers on the side.