This Chicago Style Beef Sandwich is an Italian creation originating in Chicago sometime in the 1930’s. I made mine with a slowly braised chuck roast, shredded like pulled pork, and then topped with the ubiquitous roasted peppers and of course, giardiniera. All of this deliciousness is served on a soft bun with a good amount of the pan juices for dunking. Keep the leftovers and make my equally delicious Birria Beef Tacos.
Tip : Keep the leftover beef to make delicious Birria Beef Tacos.
Ingredients
Braised Beef
- 3 lb boneless beef chuck or blade roast
- kosher salt and freshly ground black pepper
- 1 tbsp olive oil
- 1 medium yellow onion
- 1 tbsp dried oregano
- 1 tbsp dried thyme
- 1 whole poblano or banana pepper
- 6 cloves of chopped garlic
- 1/2 cup dry red wine
- beef stock
Roasted Peppers
- 1 red bell pepper
- 1 green bell pepper
- 1 tbsp olive oil
- kosher salt and freshly ground black pepper
Sandwich and Garnish
- 1 panini or sub-style bun per person
- 2-3 tbsp shredded beef per bun
- 2-3 strips roasted pepper per bun
- 1-2 tbsp giardiniera
- 1/2 cup pan juices for dipping
Instructions
Gather all ingredients before starting recipe.
Braising Beef
- Season a 3 lb boneless beef chuck or blade roast with kosher salt and freshly ground black pepper and set aside for up to an hour before braising.
- Preheat oven to 300 °F
- Heat a Dutch oven or a roasting pan with a tight-fitting lid over medium high heat for 1-2 minutes. Add 1 tbsp olive oil and heat for another 1-2 minutes.
- Add the seasoned beef and sear evenly on all sides. About 4-5 minutes per side.
- Remove beef to a plate and add 1 tbsp olive oil and 1 medium yellow onion, chopped and stir until the onions begin to brown. About 5-6 minutes.
- Add 1 tbsp dried oregano, 1 tbsp dried thyme, 1 whole poblano or banana pepper and 6 cloves of chopped garlic and stir to combine. Cook for another 1-2 minutes or until the garlic becomes fragrant.
- Add 1/2 cup dry red wine, stir scraping up all the brown bits and cook until the wine has reduced by half, about 5 minutes.
- Return the seared beef to the pan placing it on top of the vegetables. Add enough beef stock to come up about 2/3 of the way to the beef, but do not cover it all the way.
- Cover the pan with a tight‑fitting lid and transfer it to a preheated oven. Braise for 2 hours, then check the beef, it should be tender and pull apart easily with a fork. Remove the lid and continue cooking for another 30 minutes to concentrate the sauce and finish the braise.
Roasting Peppers
- When you are on the final 30 minutes of cooking the beef, place 1 red bell pepper and 1 green bell pepper, seeded and sliced on an aluminum lined cookie sheet. Drizzle with 1 tbsp olive oil and season with kosher salt and freshly ground black pepper.
- Place the peppers in the oven alongside the beef and roast for 15-20 minutes, or until the edges begin to brown and the peppers are soft. Remove from the oven and set aside until you’re ready to use them for the sandwiches.
Preparing the Dipping Sauce
- Once the beef is done, remove it to a baking sheet and cool slightly. Using two forks, shred the beef as you would pulled-pork.
- Strain the remaining pan juices through a fine sieve into bowl. Press the remaining vegetables through the fine sieve into the sauce below. Discard any vegetables left in the sieve. Degrease the surface using a spoon and set aside until ready to serve.
Assembling the Sandwich
- Cut 1 panini or sub-style bun per person in half lenghtwise.
- Using a pair of kitchen tongs, layer 2-3 tbsp shredded beef per bun as the bottom layer of the bun. Top the beef with 2-3 strips roasted pepper per bun and 1-2 tbsp giardiniera.
- Pour 1/2 cup pan juices for dipping into a small bowl and serve with the sandwich.
