Chicago's Italian Beef Sandwich: 3 Must-Try Spots

It's not difficult to find a great Italian Beef Sandwich in Chicago. But why settle for just one? Discover three Chicago Italian Beef sandwiches that you simply cannot miss.

Italian Beef Sandwich in ChicagoPhoto by2foodtrippers

Chicago's Italian Beef Sandwich is hot - both literally and figuratively. If you've watched The Bear, then you know why this classic Chicago food has recently achieved zeitgeist status.

Set in an Italian Beef Sandwich shop, the groundbreaking show's fictional depiction of life in a professional kitchen cast a large shadow over our most recent Chicago trip. This wasn't our first trip to Chicago but somehow we had missed eating the iconic sandwich during our previous swings through the windy city.

Were we previously too focused on eating Chi-dogs? Perhaps. But that's no excuse - every Italian Beef shop seems to sell excellent versions of Chicago's famous loaded hot dog so there's no need to choose one over the other.

Either way, eating a Chicago Beef Sandwich was a top food goal during our most recent visit to the mid-western megacity. After biting into just one Chicago Italian Beef sandwich, we realized that these meaty monsters hit our culinary sweet spot. We then proceeded to eat several more just to be sure.

What Is an Italian Beef Sandwich?

Despite its name, the Italian Beef Sandwich is an all-American sandwich with deep Chicago roots.

For the uninitiated, it's basically a long roll that's filled with thinly sliced roast beef. Chicago cooks follow local tradition by cooking seasoned roast beef in water and keeping it warm in its own juices on a steam table. The meat's jus becomes part of the sandwich, adding a juiciness that's not so different from the jus in a French Dip.

This jus makes ketchup and mustard obsolete. Locals skip those condiments and instead pile on sweet peppers and/or spicy, pickled giardiniera, both of which provide additional color and flavor.

Chicago Italian Beef vs. Philly Cheesesteak
It would easy to confuse an Italian Beef Sandwich with a Philly Cheesesteak until you taste the two. That's when you'll realize that the two meat sandwiches are their own beautiful things. The meats are different. (Italian Beef contains more top round compared to a Philly cheesesteak's thin sliced ribeye.) The cooking method is different. (The meat in an Italian Beef is wet roasted while cheesesteaks are fried on a flat top.) The rolls are different. The cheese is different. Even the toppings are different.

Brief History of the Italian Beef Sandwich in Chicago

Once we decided to dive deep into Italian Beef territory, it only made sense to dig into the history of the iconic Chicago sandwich too. Sadly, our history research was less successful than our eating research. We simply couldn't find a definitive answer to who exactly invented the sandwich icon.

Our favorite Italian Beef origin story involves Al Ferreri, Al's #1 Italian Beef's original owner, repurposing leftover meat from a wedding in 1938. However, while we can verify that Ferreri's original shop was located on Taylor Street, that story appears to be more legend than fact.

Either way, it's clear that Chicago's Italian Beef was invented in the 1930s around the same time that Philly's Cheesesteak and New Orleans' Po Boy made their debuts. Not only do all three sandwiches have similar origin stories involving urban entrepreneurs and hungry workers, but they're all more popular now than almost a century ago.

Unlike the Po Boy and Cheesesteak, the Italian Beef Sandwich lived under the radar beyond its Chicagoland borders for decades. Although displaced natives like the late John Belushi and former late night host Jay Leno sang its praises, it took the TV show The Bear to raise the sandwich to national attention.

How to Order an Italian Beef Sandwich in Chicago

Ordering an Italian Beef Sandwich in Chicago can be daunting unless you know the sandwich's not-so-secret language. We got lucky when Christopher Zucchero explained it to us in words we could understand. Now it's our turn to do the same for you.

First, you need to decide if you want your sandwich to be dry, wet or dipped. In other words, you're deciding whether you want your sandwich to be totally messy (i.e. dipped in jus), kind of messy (i.e. wet with some jus) or dry (i.e. dry as a doorknob). This decision comes down to whether you care more about keeping your clothes clean or eating a delicious sandwich.

Pro Tip: Don't be confused if the word 'gravy' comes up when you're ordering a Italian Beef Sandwich. In Chicago, gravy is just another word for jus.

Next, you need to decide if you want your sandwich topped with sweet peppers or hot peppers. Sweet peppers are basically sautéed bell peppers while the hot peppers option, also called giardiniera, is a flavorful melange of pickled vegetables that's oddly reminiscent of Amish chow chow.

You could go even further down the Italian Beef rabbit hole by adding cheese (typically provolone or mozzarella) and/or Italian sausage (which technically turns the sandwich into a combo). If you do, let us know how that goes.

We like to order our Italian Beef Sandwiches dipped and topped with hot peppers. Sometimes we go crazy and add sweet peppers too. Needless to say, we care more about our taste buds than we do about our laundry.

Pro Tip: Don't use the phrase "dragged through the garden" when you order an Italian Beef Sandwich in Chicago. As we learned the hard way, that phrase is specific to ordering a Chi-Dog with all the fixings and doesn't apply to ordering Chicago beef sandwiches.

Where to Eat Awesome Italian Beef Sandwiches in Chicago

Our quest to find the best Chicago Italian Beef Sandwich commenced mere hours after we landed at Midway. That late-night stop was the first of a week-long food crawl that also included Chicago-style pizza, hot dogs and donuts. But, without exaggerating, eating multiple meat-filled sandwiches was our number one priority.

This culinary journey took us deep into the Chicago cheap eats food scene and introduced us to both passionate cooks and hungry locals. While it was impossible for us to eat every contender for the best sandwich in town, we ate enough to know the good ones when we tasted them.

These are our favorite Italian Beef Sandwiches in Chicago and the ones you shouldn't miss:

1. Mr. Beef on Orleans

Mr. Beef soared to the top of our Italian Beef Sandwich radar after we watched the The Bear. Though it has a starring role on the hit Hulu show, we're pleased to report that the local institution remains close to its roots.

To be clear, Mr. Beef is the real deal despite its recent brush with fame. The down-and-dirty sandwich shop feels like it's been a fixture on Orleans Street forever or at least before 1978 when Joseph Zucchero opened the barebones River North sandwich shop with his brother Dominic.

We spotted Joseph during our visit but it his was his son Christopher's colorful commentary that brought Mr. Beef to life. As the younger "Little Mr. Beef" explained to us, this is a place where you could be sitting next to a sanitation worker or Keith Richards depending on the day. We didn't sit by either but who's to say we would have noticed if we had. Our attention was fully focused on our lunch.

Pro Tip: Mr. Beef on Orleans is no longer a late night Friday and Saturday hangout as it was prior to the pandemic. The joint currently closes at 4pm every day except for Sunday when it's closed.

Color us surprised when we realized that Mr. Beef was just a 10-minute walk from our hotel.

The short queue of locals moved quickly during our late morning visit. Before we had time to check out all of the celebrity photos displayed in the ultra-casual 'elegant' dining room, we were eating our dipped sandwich topped with hot and sweet peppers and washing it down with ice cold root beer.

We can't call the beef sandwich at Mr. Beef the prettiest we ate though it certainly was the messiest with slabs of roasted green peppers and chunks of spicy celery toppings over layers of sliced beef. However, when it comes to this type of sandwich, messy means juicy and juicy means delicious.

Mr. Beef on Orleans is located at 666 N Orleans Street, Chicago, IL 60654, United States.

2. Al's #1 Italian Beef

Famous for being one of the original Italian Beef Sandwich stands, if not the original, Al's #1 Italian Beef hasn't change much since its beginning. It still makes its sandwiches with a savory meat mixture cooked with a secret blend of spices and serves them to hungry crowds.

Visiting the original Al's in Little Italy is a trip down memory lane for many while others are happy to chow down at one of its other Chicagoland locations. We fit into the second category when we ate at an Al's stand near Wrigley Field.

Pro Tip: Order Beef in a Cup if you have a wheat intolerance or simply don't want to eat bread.

Beyond providing Wet and Dipped options, Al's also provides instructions on how to properly eat its meaty sandwich. Called The Italian Stance, this recommended technique involves standing at the counter and stuffing one's face directly into the sandwich.

While we appreciate the recommended technique's goal of minimizing drippage, we chose to sit at a table instead. And guess what? Our sandwich tasted just fine. In fact, our baguette stuffed with thinly sliced meat and a pile of crunchy giardiniera tasted great.

Al's #1 Italian Beef has multiple locations. We ate at the Al's #1 Italian Beef located at 3420 N Clark Street, Chicago, IL 60657, United States.

3. Portillo's Hot Dogs

Although Portillo's was literally the first stop on our Chicago food crawl, we didn't expect to love the place. Filled with kitsch, its ginormous River North eatery feels like a theme park - rarely a good sign when it comes to food.

Adding fuel to our doubt, Portillo's is no longer local since Dick Portillo sold his self-named Chicago restaurant to Berkshire Partners in 2014. Plus, it has the words Hot Dogs and not Italian Beef in its name. But it was open late and we were hungry. How bad could it be?

As we quickly realized, Portillo's isn't bad at all. In fact, its Italian Beef Sandwiches are great.

Pro Tip: Head to Villa Park if you want to visit the original Portillo's Hot Dog stand that opened in 1963.

Entering the cavernous Portillo's on Ontario Street can be overwhelming for first time Italian Beef Sandwich eaters. However, the fast-casual restaurant is easy to navigate since its menu spells out three ways to order - Dry, Extra Gravy and Dipped. Sweet and hot peppers are available but involve a surcharge. Order the peppers anyway.

You'll probably want to order a hot dog and fries too. At least that's what we did during our late night visit. It was all good but it was the dipped Italian Beef sandwich that we loved most. Loaded with meat and garnished with colorful giardiniera, that juicy sandwich became a base standard to which we compared all others.

Portillo’s Hot Dogs has multiple locations. We ate at the River North location at 100 W Ontario Street, Chicago, IL 60654, United States.

This article was originally published on 2foodtrippers. Consider subscribing to 2foodtrippers if you enjoyed it.