Chicago-Style Italian Beef Sandwich

The first time I encountered an Italian Beef sandwich, I was skeptical about the concept of dipping meat into more liquid before taking a bite. But watching my Chicago-born friend drag that roll through the juices, I quickly understood what the fuss was about. Now, this sandwich has become my go-to comfort food, especially on those grey Sunday afternoons when you need something to warm you from the inside out.

Last winter during a snowstorm, I made a triple batch for neighbors who had just welcomed a new baby. They texted me two hours later saying they'd never felt more cared for by a meal in their lives, and honestly, something about a sandwich this messy and wonderful just says you're in good hands.

Ingredients

• 3 lbs beef chuck roast: Chuck roast has enough marbling to stay juicy through hours of cooking and becomes incredibly tender when braised properly
• 1 tbsp olive oil: A good sear creates those flavorful browned bits that become the foundation of your entire gravy
• 1 tsp kosher salt and 1/2 tsp black pepper: This simple seasoning base penetrates the meat during cooking for flavor throughout
• 2 cups beef broth: Use a quality broth since this becomes the primary flavor of your dipping juices
• 1 cup water: This extends the liquid without overwhelming the beef flavor
• 1 tbsp Worcestershire sauce: Adds that essential umami depth that makes the au jus taste like it came from a restaurant
• 1 tbsp dried Italian seasoning: The classic herb blend that gives this sandwich its namesake flavor profile
• 1 tsp garlic powder and 1 tsp onion powder: These dried aromatics dissolve beautifully into the cooking liquid
• 1/2 tsp crushed red pepper flakes: Optional heat for those who like their beef with a little kick
• 1 bay leaf: The secret background note that makes people wonder what makes this taste so authentic
• 6 sturdy Italian sandwich rolls: You need rolls that can stand up to serious dunking without falling apart completely
• 1 1/2 cups hot giardiniera: Chicago-style pickled vegetables bring the essential crunch and vinegar brightness
• 1 cup roasted sweet bell peppers: These add a mellow sweetness that balances the sharp giardiniera

Instructions

Sear the beef with confidence:

Pat that chuck roast completely dry with paper towels, then season it all over with salt and pepper. Heat your olive oil in a large Dutch oven over medium-high heat until it shimmers, then add the beef and sear every side until deeply browned.

Build your braising liquid:

Pour in the beef broth, water, Worcestershire sauce, and all those dried herbs and spices. Tuck in the bay leaf and bring everything to a gentle simmer while scraping up any browned bits from the bottom.

Let time do the work:

Cover your pot and either transfer to a 325°F oven for 4 hours or set your slow cooker to low for 8 hours. Flip the beef once halfway through, and trust the process until the meat offers zero resistance when poked.

Shred and reunite:

Remove the beef to a cutting board and let it rest for 10 minutes while you skim any excess fat from the surface of your cooking liquid. Use two forks to shred the meat, discarding any large pieces of fat, then return it all to the pot to soak up those juices.

Assemble like a pro:

Split your rolls and give them a quick toast if you like some crunch. Pile that juicy beef high on each roll, spoon over a generous amount of au jus, then top with a mountain of giardiniera and those roasted peppers.

Save

My dad still talks about the Sunday I made these for his birthday dinner. He'd never heard of an Italian Beef sandwich before, and watching him navigate that first messy bite with juice running down his chin has become one of my favorite kitchen memories ever.

Making It Ahead

The beef actually develops deeper flavor when made a day ahead, and the fat separates easily from the cold au jus for skimming. I often cook it on Saturday and let it chill overnight, then gently reheat everything before serving. Just don't assemble the sandwiches until you're ready to eat or you'll end up with soggy bread.

The Bread Situation

Not all rolls are created equal when it comes to Italian Beef. I've learned the hard way that soft sandwich rolls turn into mush immediately. You want something with a substantial crust that will hold its structure through that crucial dip in the juices. Local Italian bakeries usually have the best options, but a sturdy hoagie roll works perfectly fine too.

Customization Ideas

While the classic preparation is pretty perfect, I've discovered some wonderful variations over the years. Sometimes I add provolone cheese to melt over the hot beef, and during summer I'll swap in fresh giardiniera vegetables for the jarred version. The slow cooker method frees up your oven and works beautifully if you're out of the house all day.

• Try adding a splash of red wine to your braising liquid for extra depth
• Mild giardiniera makes this more kid-friendly while still keeping that signature crunch
• Cut your rolls in half and serve sliders for your next party spread

Save

There's something wonderfully communal about gathering around a table with napkins aplenty and sandwiches this messy. It's not fancy food, but it's the kind of meal that turns strangers into friends and makes regular days feel like celebrations.

Questions & Answers

→ What makes this Chicago-style?

Authentic Chicago-style sandwiches feature thinly sliced or shredded beef that's been slow-cooked in seasoned broth, served on Italian rolls with giardiniera and dipped in au jus—the defining elements since the 1930s.

→ Can I make this in a slow cooker?

Absolutely. Cook on low for 8 hours or high for 4-5 hours until the beef shreds easily. The results are just as tender and flavorful as oven braising.

→ What is giardiniera?

A Chicago-style pickled vegetable mix typically containing cauliflower, carrots, peppers, and celery marinated in oil and vinegar. Choose hot or mild depending on your spice preference.

→ How do I prevent soggy bread?

Use sturdy Italian rolls that can hold up to the juices. Toast them lightly before assembling, and don't over-dip—just a quick dunk in the au jus adds flavor without making the bread fall apart.

→ Can I add cheese?

Provolone is the traditional choice. Add slices during the last few minutes of heating so they melt over the beef, or place cheese directly onto the toasted rolls before piling on the meat.

→ How should I store leftovers?

Store shredded beef and au jus separately in the refrigerator for up to 4 days. The flavors actually improve overnight. Reheat gently in the juices before serving for best results.