Skydeck-Inspired Chicago Italian Beef Sandwich

By AislePrompt Test Kitchen · Reviewed by AislePrompt Editorial · ·

Slow-cooked Italian beef with a savory au jus, piled high on a soft hoagie roll for a classic Chicago street food experience. This american-inspired sandwiches & wraps ready in about 200 minutes pairs beef chuck roast, garlic cloves, minced, dried oregano for a weeknight-friendly dinner that comes together with one pan and minimal cleanup. Each serving lands at about 650 calories and feeds 4, 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.

★ 4.3 (13 ratings) Prep: 20 min Cook: 180 min Serves 4 American cuisine 650 cal/serving
Plan a meal with the AI →

Ingredients

Instructions

  1. Step 1: Preheat oven to 325°F. Rub 3 lbs beef chuck roast with 4 minced garlic cloves, 1 tsp dried oregano, 1 tsp dried basil, 1/2 tsp dried thyme, 1 tsp salt, and 1 tsp black pepper evenly.
  2. Step 2: Heat 2 tbsp olive oil in a large oven-safe pot over medium-high heat. Sear the beef roast on all sides until browned, about 3 minutes per side.
  3. Step 3: Add 2 cups beef broth, 6 sliced pepperoncini peppers, and 2 tbsp soy sauce to the pot with the beef. Bring to a simmer, cover, and transfer to the oven.
  4. Step 4: Cook for 3 hours until the beef is tender and shreds easily with a fork.
  5. Step 5: Remove the beef from the pot and shred with two forks, reserving the cooking liquid (au jus).
  6. Step 6: Slice 4 hoagie rolls horizontally but not completely through. Pile each with shredded beef and top with 1 slice provolone cheese.
  7. Step 7: Toast sandwiches in a 375°F oven for 5 minutes until the cheese melts and the rolls are warmed.
  8. Step 8: Serve sandwiches with warmed reserved au jus for dipping.

Frequently asked questions

How long does Skydeck-Inspired Chicago Italian Beef Sandwich take to make?

Total time is about 200 minutes (20 min prep + 180 min cook). Most home cooks find this fits comfortably into a weeknight; double the batch on Sunday for two dinners.

How do I store leftover Skydeck-Inspired Chicago Italian Beef Sandwich?

Cool to room temperature within 2 hours, then store in an airtight container in the fridge for up to 4 days. Reheat covered in a 350°F oven for 10-12 minutes, or microwave at 70% power in 60-second bursts to keep beef chuck roast from drying out.

Can I substitute ingredients in Skydeck-Inspired Chicago Italian Beef Sandwich?

Yes — most ingredients in this recipe have flexible swaps. For oil, use any neutral high-smoke-point oil (avocado, grapeseed, refined coconut). For aromatics, dried herbs at ⅓ the volume of fresh work in a pinch. The full ingredient list is shoppable on Instacart so you can see substitutes in real time.

How do I scale Skydeck-Inspired Chicago Italian Beef Sandwich for a different number of people?

The recipe is written for 4 servings. Multiply each ingredient by (your serving target / 4). Cook time stays roughly the same up to 2x; for 3-4x batches, switch from a skillet to a sheet pan or stockpot so the food isn't crowded — overcrowding steams instead of browns.

What goes well with Skydeck-Inspired Chicago Italian Beef Sandwich?

American sandwiches & wraps like this pair well with a simple grain (rice, couscous, or crusty bread), a quick salad with acid (lemon vinaigrette, pickled onions), and a pan sauce or yogurt-based dip. Tap "Plan a meal with the AI" to get specific side suggestions.

What others are saying

Related recipes