10 Portillo's Menu Items, Ranked

Forget deep dish pizza. For many Chicagoans, the city's true culinary claim to fame lies in the iconic street foods — think gourmet hot dogs, Polish sausages, and Italian beef sandwiches. The Windy City is a melting pot of different flavors, and many come together under one roof at Portillo's.

It's been an institution in Chicago and beyond since 1963. But for those of us who didn't happen to grow up in the area, it's more of an enigma. When you hear locals talk about it, they'll boldly say "you have to get this" or "you have to get that." You might overhear strange things about dipping a sandwich or "dragging a dog through the garden." And when you walk in, you'll see Italian-style checkered tablecloths paired with quirky vintage memorabilia. Perhaps not that unusual, but the atmosphere still adds to the intrigue.

Between the unfamiliar lingo and the endless opinions, it's a lot to take in. So the best approach as a Portillo's newbie is to take it all at face value. For me, that meant trying 10 of the chain's most popular items for myself. Now, I'm not a true first-timer, but with just a few one-off visits under my belt, I could still approach this with a fairly fresh lens. I grabbed my husband and a couple of friends to help me sample the menu. Then, I ranked all 10 items based on flavor, legendary appeal, and how likely I'd be to order them again.

I have so many questions about this bowl. But I think this one sums it up best: What the heck is going on here? When I read the word "bowl," I assumed there would be some kind of base like greens, grains, maybe even pasta. But no. The Chicago Combo Bowl is made up of just slow-roasted Italian beef (the same kind you would find on a Portillo's sandwich) and a cut-up Italian pork sausage. Then, you have the option to tack on shredded cheese and either sweet or hot peppers, or both. I tried to spice mine up with both kinds of peppers, but apparently that request never made it to the kitchen. I wound up with just a bowlful of meat that both looked and tasted as sad as it sounds.

The Italian beef feels out of place with no bread surrounding it. The juices have nowhere to go, so they pooled at the bottom, and the savory flavor felt milder than ever. The sausage is better. It's thick and juicy with more to offer in terms of taste. But the Italian spice notes could be stronger. It just an odd choice. A slop bowl of sorts. And priced the same as a full Italian beef sandwich, it feels like highway robbery.

It's not a bad burger. It just feels like an afterthought — like Portillo's was trying to fill one more spot on its menu and quickly decided on burgers (that goes with Chicago-style hot dogs and Italian beef, right?). Then, just as hastily, the chain threw together the recipe.

The burgers do come char-broiled, which is an initial selling point. The open-flame cooking method is supposed to produce char marks and a deeper, smokier flavor. But with a conveyor belt system in place, the process looks less glamorous in person and resulted in a patty that was well done and not remarkably flavorful. I ordered my single cheeseburger with everything on top, which included lettuce, tomato, red onion, pickles, mayonnaise, and ketchup. I was thankful the toppings were there to spruce it up a bit. At the same time, though, they didn't work any miracles to significantly enhance the sandwich. The thick globs of condiments were also a nuisance.

The bun itself was the final straw. It's the standard at Portillo's to plop its classic burgers on an old-fashioned bun that's dusted with cornmeal. I appreciate the old-school touch, but it's not doing this handheld any favors. If anything, it makes the burger seem dry and even more muted. I would have much preferred a standard or brioche bun.

The cheese fries aren't just a Portillo's side; they're the Portillo's side. Though, to be fair, they don't have a whole lot of competition — up against onion rings, chili, a side salad, and a list of miscellaneous à la carte items.

The fries are of the crinkle-cut variety, and the cheddar cheese sauce is served on the side for dipping purposes rather than smothered on top. I appreciate this because then you don't have to deal with sogginess. Overall, they're good, but in the way that most cheese fries are good. And I was actually a little disappointed. The fries land somewhere between crisp and limp with what feels like just a haphazard shake of salt over the top. 

As for the cheese, it's only a small step above your basic concession stand nacho cheese. It's just a smidge sharper with a less obvious processed flavor. Together, the fries and cheese make for a semi-satisfying bite. I'd put them on par with most other fast food cheese fries from chains like Culver's or Shake Shack — though I actually think I prefer Shake Shack's cheese a bit more. Would I order them again? Probably. Especially over the bowl or cheeseburger. But I expected more.

Portillo's gives you the option to order its chicken tenders in quantities of four, six, or 20. For the sake of sampling, I went with the smallest order of four, and honestly that was enough for just me. These are some sizable tenders. Paired with a side of fries and a drink, it would have been a filling meal.

The breading was clearly applied thick and hits you with that audible crunch when you bite into it fresh. It reminded me a bit of KFC's famously finger-lickin' breading. But without the proprietary blend of 11 herbs and spices, and with a much lower level of greasiness. Inside, the real white meat chicken is plump, and I'd say the ratio of breading to meat is just about what you want. By themselves, the tenders still come off a bit dry, though.

They're solid. They're just not the most exciting thing on the menu. I do, however, have a soft spot for the sauces. The chain gives you plenty to work with. It allows you to pick two kinds, even just for four tenders, and I received two cups of each. It was like a saucy dream. Of course, I had to try the chain's Comeback and Hot Giardiniera sauces. Just like a tangier Raising Cane's sauce, the Comeback sauce was an instant hit at the table. Creamy, zesty, and spicy, thanks to the hot vegetable relish, the Giardiniera is no slouch either.

It's a Portillo's staple paying homage to the Windy City's way of doing hot dogs. This isn't your minimalist frank and bun plucked from a NYC cart on the corner of Broadway and 42nd. This is an extravaganza of bright toppings. It's the "everything and the kitchen sink" version of a hot dog.

Just on the condiment side, you have mustard, relish, and celery salt. Then come the veggies, which include diced onions, sliced tomatoes, an entire kosher pickle spear, and sport peppers. Anchored by a poppy seed bun and, of course, the beef hot dog (yes, there is one hiding under there), it makes for quite the colorful display. Apparently in Chicago, this is referred to as "dragging the dog through the garden". The logic checks out.

As crazy as it looks, it's a good assemblage of toppings. I especially like the extra fresh relish and the tang coming at you from all angles. It's flavorful without going over the top, as I feared it would. I can see why it's a favorite and immediately gave it a spot above items like the tenders and fries. Where it lacks ever so slightly is the hot dog itself. As it turns out, underneath the garden of garnishes, it's pretty humdrum, lacking the bold savory flavors I would expect from an all-beef frank. Without its toppings, it would be nothing (well, maybe not nothing, but not nearly as good).

No, this salad couldn't possibly compete with some of Portillo's most iconic items (the items that are still to come). On that front, it was already behind before the race had even begun. But as far as restaurant salads go, it's a refreshingly tasty pick.

It has just as many ingredients as the Chicago hot dog, and the best way I can describe it is like some kind of hybrid between a cobb salad and a pasta salad. The base is made up of one-part romaine and iceberg lettuce mix and one-part ditalini pasta, giving it more substance than your run-of-the-mill chopped salad. Diced grilled chicken and bacon crumbles make it even more wholesome, and the color comes from a combination of tomatoes, green onion, red cabbage, and, my personal favorite addition, gorgonzola cheese crumbles. Give me some stinky cheese and some protein in a salad, and I'm on board. You have bright flavors in this bowl, coupled with smoky and savory. And, of course, no salad is complete without a complementary dressing. Portillo's house recipe is like an Italian vinaigrette that's sweeter and more garlic-forward.

I would, without a doubt, order this again. I would also venture to guess that the new Spicy Chopped Chicken Salad is just as good, if not better. It cranks things up a notch with crispy spicy chicken and hot Giardiniera peppers.

"Let them eat cake" — said probably the Portillo's head honchos after creating an entire menu of hearty Chicago street food. Chocolate cake is not necessarily the kind of dessert you would expect at a fast-casual chain like this. It's usually reserved for steakhouses and more polished sit-down restaurants. But Portillo's breaks the mold, and we're grateful that it chooses to be different.

Even just a single slice of the cake is monstrous — shareable amongst three to four people for sure. Each one is homemade fresh in the restaurant each morning. It's double-layered, and every single cake receives the royal treatment of two total pounds of frosting. The first thing I noticed about the cake was the fluffy, almost cloud-like texture. It all but melts in your mouth when you take a bite. Apparently mayonnaise is the secret ingredient used to help create this dreamy, tender crumb (don't worry, you can't taste the condiment). What you do taste is a rich cocoa flavor, always supplemented by a ribbon of dense, fudgy frosting. It's the definition of a sinful dessert.

Its pure indulgence gets it far, and certainly farther than the chopped salad. If you ever see me picking a salad over a slice of cake, please stop and ask if I'm okay. The only downside is that it's a pretty heavy choice after an equally heavy meal. It may just push you over the edge.

You have some options when it comes to Portillo's pride and joy: the Italian beef sandwich. Each sandwich does start the same way with a base of freshly-baked Turano French bread and a heap of thinly-sliced, slow-roasted Italian beef. But then comes the fun part. You get to choose your level of "wetness." Yes, it sounds weird, but it simply has to do with how much of the chain's savory meat gravy is added to your sandwich. The options range from dry all the way up to "dipped," where the entire thing — bun and all — is dunked into the vat of au jus. And we're not done yet. You also get to pick your peppers and a cheese to go on top, if you so choose.

I had to see what the dipped sandwich had to offer and finished mine off with both sweet and hot peppers. Let me tell you, this thing was SOGGY. It was disintegrating on contact, but I couldn't help but enjoy the rich salty flavors. The crunch of the peppers helped to offset the softer textures of the soaked meat and bread, and also cut through the onslaught of savoriness. It's one of the most satisfyingly messy sandwiches you're likely to find. However, I do think it could benefit from a bold condiment. The chain's hot Giardiniera seems like the natural pick.

Chicago's Polish influence pops up on the Portillo's menu as well. You'll find it in the form of Polish sausages, including this Maxwell Street classic – named for the Chicago street it was born on over 75 years ago. It's actually produced by Makowski's Real Sausage Company. But it's not until it reaches Portillo's that it's grilled, plopped into a sesame seed hot dog bun, and topped with a generous amount of yellow mustard and grilled onions.

If I'm going the frank route at Portillo's, I'm picking this over the hot dog every time. I don't care if the dog is covered in every single garnish under the sun. A pork sausage with a bigger, juicier, meatier flavor will always come out on top. It takes on all those salty, smoky, garlicky notes of a traditional kielbasa, making it far more flavorful than a classic hot dog or even something like a German bratwurst.

It's a sausage good enough to eat on its own with a fork, but the toppings make it even better. They feel simple, yet intentional. A classic, no-frills yellow mustard gives it that subtle zing, while the cooked-to-perfection silky onions offer a touch of sweetness. Delivered on a spotted and soft sesame seed bun, it comes in as one of my favorite Portillo's items — surprisingly beating out the Italian beef with what I thought was a more intriguing combination of flavors.

It's everything you love about the chocolate cake but 10 times better. This isn't just a milkshake made up to taste like chocolate cake — perhaps with some chocolate syrup or hot fudge swirled into the ice cream. No, that's far too boring. Portillo's is crazy enough to take an actual slice of its famous chocolate cake and cram it right into the blender to create a different kind of chunky, drinkable confection.

At first, I didn't think I would like bits floating in my milkshake. But as it turns out, I ABSOLUTELY LOVED IT. In this new format, you still get to enjoy all those super rich, fudgy flavors of the cake. But it's mellowed out by the softer notes of vanilla ice cream, so it's not so intense and food coma-inducing. It's thick, and you get those fine saturated cake crumbs in every swig. I would recommend giving it a swirl with your straw from time to time to keep all the cake from settling at the bottom. Unless, of course, you're looking forward to scooping up the last bits of milk-logged cake with a spoon.

I couldn't get enough of this shake. My husband couldn't get enough. My friends couldn't get enough, and at the end of our Portillo's feast, we were all in agreement that the shake was the highlight of the entire meal.

As I mentioned, I'm not from the Chicago area, and Portillo's has yet to expand its reach to my city of Columbus, Ohio. So, it took a road trip to Indianapolis to get my hands on these items. Before I started the journey, I did some quick research into what Portillo's foods are most popular and what's worth trying. I landed on 10 total items, ranging from sandwiches to sides to desserts, and sat down to a giant meal with help from a few others.

I'm aware that there are some very different things on this list. Comparing an Italian beef sandwich to a chocolate cake shake is messy business. Sure, they all pay tribute to Chicago's food history, but they're also wildly different. So I had to focus most of my rankings purely on taste and how happy it made my taste buds. I looked for well-cooked ingredients, great flavor combinations, and originality never hurt either. It came down to items that I not only could see myself ordering again, but also items that I will find myself craving periodically until I make my way back to Indy — or even better, the chain's birthplace of Chicago.