Italian Beef Sandwich Chicago Style

My first Sunday in Chicago, I followed the smell of spiced beef down an alleyway behind a grocery store in Little Italy. A guy in an apron passed me a sandwich wrapped in wax paper through a back door, and somewhere between that first bite and finding juice dripping down my sleeve, I understood what everyone meant about this city. The roll had surrendered completely to the broth but somehow still held everything together. That messiness is the whole point.

I made these for a watch party during the Bears season, and people kept grabbing napkins before even sitting down. My friend Sarah actually stood at the counter eating hers because she refused to risk staining her couch, but she went back for seconds anyway. Something about having your hands full of this sandwich makes conversations happen around the kitchen island instead of the living room.

Ingredients

• 3 lbs beef chuck roast: Chuck has enough marbling to stay juicy through hours of cooking, and it shreds into those perfect tender strands that soak up all the spices
• 1 tbsp olive oil: You want just enough to get a good sear going without making the beef greasy
• 1 tsp kosher salt and 1/2 tsp black pepper: Simple seasoning that lets the other flavors shine without competing
• 2 cups beef broth and 1 cup water: The broth builds depth while the water keeps everything from becoming too intense as it concentrates
• 1 tbsp Worcestershire sauce: This adds that subtle umami background that makes people ask what your secret ingredient is
• 1 tbsp dried Italian seasoning: The classic herb blend that gives this its signature aroma
• 1 tsp garlic powder and onion powder: Use powder instead of fresh here, they dissolve into the cooking liquid better
• 1/2 tsp crushed red pepper flakes: Optional, but that gentle heat builds as it cooks
• 1 bay leaf: Old school, but it adds a subtle herbal note that balances the richness
• 6 sturdy Italian rolls: Flimsy bread will disintegrate, you need rolls with some backbone
• 1 1/2 cups hot giardiniera: Chicago style means the vegetables are chopped small and packed in oil
• 1 cup roasted sweet bell peppers: These add sweetness that cuts through the spice and beef

Instructions

Sear the beef until it is deeply browned:

Pat the roast completely dry with paper towels, season it with salt and pepper, then sear in hot oil until every side has a dark caramelized crust. This creates the foundation of flavor that simmers into the broth.

Build the braising liquid:

Pour in the broth, water, Worcestershire, Italian seasoning, garlic and onion powders, red pepper flakes, and bay leaf right into the pot with the beef.

Let it cook low and slow:

Cover and braise in a 325°F oven for 4 hours or in a slow cooker on low for 8 hours, flipping the beef once halfway through. You will know it is done when it offers zero resistance when you poke it.

Shred and reunite the beef:

Rest the meat on a cutting board for 10 minutes, skim the fat from the liquid, then shred with two forks. Toss it back into the pot to absorb all those juices before serving.

Assemble the sandwiches:

Lightly toast the rolls if you want, pile on the beef with some jus, and finish with generous spoonfuls of giardiniera and roasted peppers.

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My dad called me after trying these, asking what restaurant I ordered them from because he refused to believe I made them myself. When I finally told him it was just a chuck roast and patience, he started making them every Sunday during football season. Some traditions catch on fast.

Making It Your Own

The beauty of this recipe is how forgiving it is. I have thrown in leftover wine, swapped in different seasonings, and even used beer instead of water when that was what I had in the fridge. Every version has worked because the method is solid.

The Bread Matters

Avoid soft sandwich rolls or baguettes that are too hard. You want something with a sturdy crumb that can hold up to the juice but is not going to fight you when you bite down. Local bakery rolls usually work better than the ones from the grocery store bread aisle.

Perfecting The Dip

The au jus should be intense enough to stand on its own but not so salty that it overpowers the beef. Taste it at the end and adjust with more broth or water if needed. Some people add a splash of vinegar or lemon juice to brighten it.

• Keep some extra jus warm in a small pitcher for people who want to really commit to the mess
• Have plenty of napkins ready, there is no elegant way to eat this sandwich
• If you are feeding a crowd, set up a sandwich bar and let people build their own

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This is the kind of food that brings people together around a table, juice running down their arms, laughing through every bite.

Your Questions Answered

→ What makes this sandwich Chicago-style?

Chicago-style Italian beef features thinly sliced or shredded beef that's been slow-cooked in seasoned broth, served on Italian bread with giardiniera and au jus for dipping. This combination creates the signature juicy, messy sandwich that Chicago locals love.

→ 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 until the beef is fork-tender. The result will be equally delicious and perfect for busy days.

→ What is giardiniera?

Giardiniera is a Chicago-style relish made with pickled vegetables like cauliflower, carrots, celery, peppers, and olives in oil and vinegar. It adds essential crunch, tang, and heat that balances the rich, tender beef perfectly.

→ How do I prevent soggy bread?

Use sturdy Italian rolls and avoid soaking them too long. For the best texture, lightly toast the rolls before filling, or quickly dunk them in au jus just before adding the beef—this adds flavor without making the bread fall apart.

→ Can I add cheese to this sandwich?

Yes, provolone or mozzarella cheese are excellent additions. Place slices on the toasted rolls under the broiler for 1-2 minutes until melted and bubbly before piling on the beef for an extra indulgent version.

→ How long do leftovers keep?

Store shredded beef separately in its cooking liquid for up to 4 days. The flavors actually develop and improve over time. Reheat gently on the stove, adding a splash of water or broth if needed. Rolls and giardiniera should be stored separately and assembled fresh.