Italian Beef Sandwich Chicago Style

The first time I had an Italian Beef sandwich in Chicago, I stood at a tiny counter near the old Comiskey Park, juice dripping down my arm, wondering why nobody had told me about this magic combination sooner. My baseball game was forgotten. The beef, so tender it practically fell apart, mixed with that fiery, crunch-filled giardiniera. I went back three times that week.

Last winter, when my cousins came over for what we called our annual fake Super Bowl since none of us actually care about football, I made these sandwiches. The house smelled like garlic and beef for hours. We ended up eating standing up around the kitchen island, napkins everywhere, arguing about who got the last cup of dipping juice.

Ingredients

• 3 lbs beef chuck roast: Chuck roast has the perfect marbling for slow cooking, becoming tender without falling apart completely
• 1 tbsp olive oil: Essential for getting that beautiful, flavorful crust on the beef before braising
• 1 tsp kosher salt and 1/2 tsp black pepper: Simple seasoning that goes a long way when paired with the cooking liquid
• 2 cups beef broth and 1 cup water: Creates the base of your au jus while keeping the beef submerged
• 1 tbsp Worcestershire sauce: Adds that deep, umami richness that defines the sandwich flavor profile
• 1 tbsp dried Italian seasoning: Provides the classic herb backbone without overwhelming the beef
• 1 tsp garlic powder and onion powder: Layered aromatics that build flavor without burning like fresh garlic might
• 1/2 tsp crushed red pepper flakes: Optional, but recommended if you like a gentle warmth underneath everything
• 1 bay leaf: Old-school secret that adds subtle depth to the braising liquid
• 6 sturdy Italian rolls: Flimsy bread will disintegrate, so get rolls that can handle serious juiciness
• 1 1/2 cups hot giardiniera: The non-negotiable Chicago element that makes this sandwich sing
• 1 cup roasted sweet bell peppers: Optional, but they add sweetness that balances all that vinegar and heat

Instructions

Season and prep the beef:

Pat the chuck roast completely dry with paper towels so it will brown properly. Sprinkle salt and pepper all over, pressing gently to help it stick.

Build a flavorful crust:

Heat olive oil in a Dutch oven over medium-high heat until shimmering. Sear the beef on all sides until deeply browned, about 3 to 4 minutes per side.

Create the braising liquid:

Pour in the beef broth, water, Worcestershire sauce, and all those seasonings. Bring everything to a gentle simmer, making sure to scrape up any browned bits from the bottom.

Slow cook to perfection:

Cover and transfer to a 325°F oven for 4 hours, flipping the beef halfway through. The beef should be fork-tender and practically falling apart when done.

Rest and shred:

Let the beef rest on a cutting board for 10 minutes so the juices redistribute. Skim excess fat from the liquid, then shred the beef with two forks.

Reunite beef and juices:

Toss the shredded beef back into the pot, letting it soak up all that flavorful au jus. Keep everything warm while you prep the rolls.

Build your sandwiches:

Split the rolls and give them a quick toast if you like. Pile on the beef generously, spooning over extra juice, then top with giardiniera and roasted peppers.

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My dad texted me at midnight after I first made these for the family, saying he was already planning next weekend around round two. That is when I knew this recipe was a permanent fixture.

Making It Your Own

Sometimes I add provolone right on the beef while it soaks in the juices. The cheese melts into every nook and cranny, creating these incredible little pockets of creamy, savory goodness. My purist friend says this is technically a different sandwich, but nobody complains when they are eating it.

The Bread Makes All the Difference

After testing every roll in three grocery stores, I learned that too-dense bread never soaks up enough juice. Too-soft bread falls apart before you finish eating. The sweet spot is a roll with some chew and structure, something that can hold its own against all that tender beef and spicy topping.

What To Serve Alongside

These sandwiches are hearty enough to be the entire meal, but a crisp green salad with vinaigrette cuts through the richness. I also keep a stack of extra napkins on the table because Italian Beef is not a neat food. That is part of the charm.

• Coleslaw with a light, tangy dressing
• Potato salad that is not too heavy
• Ice-cold beer or sparkling water

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There is something about a sandwich that requires two hands and full attention that brings people together in the best way.

Recipe Questions & Answers

→ What makes Italian beef different from other beef sandwiches?

Italian beef stands apart through its preparation method—the beef is slow-cooked and braised in its own juices with Italian seasonings, then sliced or shredded thinly and served with extra cooking liquid (au jus) for dipping. The meat becomes incredibly tender and absorbs the aromatic flavors of the broth.

→ Can I make this in a slow cooker?

Absolutely. After searing the beef, transfer everything to your slow cooker and cook on low for 8 hours or high for 4-5 hours. The results are just as tender and flavorful as the oven method, making it perfect for busy days or when you want to come home to a ready-made meal.

→ What is giardiniera and where can I find it?

Giardiniera is a Chicago-style relish of pickled vegetables including cauliflower, carrots, bell peppers, celery, and sometimes olives, marinated in oil with vinegar and spices. Look for it in the pickle aisle of well-stocked grocery stores, Italian markets, or specialty food stores. Both mild and hot varieties are available.

→ How do I prevent the sandwich from getting soggy?

The key is using sturdy Italian rolls that can handle the moisture. You can lightly toast the cut sides of the rolls before assembling. If you're concerned about sogginess, serve the au jus on the side for dipping rather than pouring it directly onto the sandwich.

→ What cut of beef works best?

Chuck roast is ideal because it has enough marbling and connective tissue to become tender and flavorful during long cooking. The long braising time breaks down these tissues, resulting in meat that shreds easily and stays moist. Avoid lean cuts like round, which may become tough and dry.