Hidden Gem Chicago-Style Italian Beef Sandwiches

By Lauren Mitchell, Test Kitchen Director · Reviewed by AislePrompt Editorial · Published 2026-06-19 · Updated 2026-06-19

Juicy, slow-cooked Italian beef slices simmered in a savory au jus, served on crusty rolls with sweet peppers for a classic Chicago street food experience. This american-inspired sandwiches & wraps ready in about 500 minutes pairs beef chuck roast, minced garlic cloves, dried oregano for a weeknight-friendly dinner that comes together with one pan and minimal cleanup. Each serving lands at about 600 calories and feeds 6, so it slots cleanly into a weekly meal plan and pairs well with a quick salad or grain on the side. Tap "Plan a meal with the AI" below to drop this recipe into your week and send the ingredients straight to Instacart. Nutrition values are approximate, calculated from USDA FoodData Central (fdc.nal.usda.gov) — verify against ingredient labels for any health-driven dietary plan.

Ingredients

• 3 lbs beef chuck roast
• 6, minced garlic cloves
• 2 tsp dried oregano
• 2 tsp dried basil
• 1 tsp crushed red pepper flakes
• 4 cups beef broth
• 1 cup, sliced banana peppers
• 1/2 cup giardiniera (Italian pickled vegetables)
• 6 Italian sandwich rolls
• 2 tbsp olive oil
• 1 1/2 tsp salt
• 1 tsp black pepper

Instructions

1. Step 1: Heat 2 tbsp olive oil in a large skillet over medium-high heat. Season 3 lbs beef chuck roast with 1 1/2 tsp salt, 1 tsp black pepper, 2 tsp dried oregano, and 2 tsp dried basil. Sear the beef on all sides until deeply browned, about 4 minutes per side.
2. Step 2: Transfer the seared beef to a slow cooker. Add 6 minced garlic cloves, 1 tsp crushed red pepper flakes, and 4 cups beef broth. Cover and cook on low for 8 hours until the beef is tender and easily shredded.
3. Step 3: Remove the beef from the slow cooker and shred it with two forks. Reserve the cooking liquid (au jus) and skim off excess fat.
4. Step 4: Place shredded beef back into the slow cooker with the reserved au jus and 1 cup sliced banana peppers. Let it warm on low for 30 minutes to absorb flavors.
5. Step 5: To assemble, split 6 Italian sandwich rolls lengthwise without cutting all the way through. Pile generous portions of the beef mixture inside each roll, topping with 1/2 cup giardiniera for a spicy crunch. Serve with small bowls of warm au jus for dipping.