Chicago Style Italian Beef

I’ve tried to cater my recipes the past week to the upcoming Thanksgiving holiday, and that was still my intention for today’s post! All was well, I was so excited to share my favorite Thanksgiving dressing recipe with you and then disaster struck.

Chicago Style Italian Beef

Chicago Style Italian BeefChicago Style Italian Beef

Well, maybe not ultimate disaster, but on a scale of 1 – Total Thanksgiving Recipe Disaster, I hit about an 8.5. I was working on a Sausage, Apple, Kale, Cornbread Dressing recipe and it was looking and smelling sooo good you guys! I even told my Mother-In-Law that I would be freezing it and bringing it to family Thanksgiving next week. Well, when your brain shuts off right as you’re pouring in your chicken broth and you realize right as you’ve poured in the last drip that you put 2-3x the amount of liquid in that you were supposed to, all you can do is wait and pray that it will magically work out.

It didn’t. It DID NOT work out at all. I had it in the slow cooker for 5 hours and then it spent 3 hours in the oven on a baking sheet trying to dry out and by that point, it had turned into large hunks of a glorified bread mush/puree. I even tried to photograph it you guys – not cool. It looked terrible and I just couldn’t do that to you guys. Honesty is the best policy, so that’s why you got the full story!

If you’re looking for a yummy stuffing recipe for next week though, check out my friend Chelsea’s Sausage Dressing with Fennel and Pears!

Chicago Style Italian Beef

As sad as I was about the dressing, I moved on. We had eaten these Chicago Style Italian Beef Sandwiches the night before and I wasn’t planning on posting them since Dressing was in the queue, but they were just too good not to share! The meat was so tender and the relish/green pepper combo gave the perfect kick. I don’t have much experience cooking with beef, so I was a bit nervous that it would be too dry or I would have somehow chosen the wrong cut at the grocery store, but it really was easy and they turned out great!

Chicago Style Italian Beef

When Kevin and I flew down to Austin back in the Spring to scout out our moving options, we ended up staying in Chicago for a night before our flight left. We visited a classic beef sandwich joint that blew my socks off and I had been thinking about it ever since! If you’re not aware of how to order an italian beef when you’re somewhere authentic, ask for “a beef” instead of “a beef sandwich” and ask for it “dry” if you don’t want it dipped in the meat juices or ask for it “sloppy or wet” if you want it dripping with the sauce. I tend to fall somewhere in the middle because I still like my bread to be in tact; Kevin on the other hand would be ok eating it from a bowl of the broth with the bread and meat just floating around in there…

This may not be in the spirit of Thanksgiving, but maybe perfect for Friendsgiving??

Switch things up a bit, get crazy!

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Chicago Style Italian Beef

  • Author: Kitschen Cat
  • Yield: 6 1x


  • 1 ½ tablespoons crushed red pepper flakes
  • 1 teaspoon red wine vinegar (affiliate)
  • 3 pickled jalapenos, thinly sliced
  • 3 ribs celery, thinly sliced
  • Kosher salt and freshly ground black pepper to taste
  • 1 tablespoon dried basil
  • 1 tablespoon dried oregano
  • 4 cloves garlic, minced
  • 2 ½ lb beef sirloin tip roast, trimmed
  • 6 crusty italian rolls, split
  • 3 green bell peppers, thinly sliced and boiled until soft


  1. Combine half the red pepper flakes, vinegar, jalapeno’s, celery, salt, and pepper in a small bowl. Cover with plastic wrap and refrigerate for 8 hours or up to overnight.
  2. Preheat oven to 425 degrees. Combine remaining red pepper flakes, basil, oregano, garlic, salt, and pepper in a small bowl. Place beef in a roasting pan or cast iron skillet and rub with half the spice mixture. Roast in oven for 20 minutes.
  3. Reduce heat to 350 degrees and roast for another 20 minutes. Mix remaining spice mixture with 4 ups of water and add to pan with roast. Continue roasting at 350 degrees until meat thermometer inserted into thickest part of the meat reads 135 degrees. Additional cooking time could range from 15-30 minutes.
  4. Transfer roast to a cutting board and let sit for 15 minutes. Keep broth warm in roasting pan.
  5. Thinly slice beef with an electric knife, deli slicer, or a sharp carving knife and return to warm meat broth. Toast your italian rolls, then stuff with beef, broth, green peppers, and top with pepper relish.


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