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DoorDash Diaries: The pleasure and plight of Portillo’s

DoorDash Diaries is a confessional cry-for-help from two Chicago-based millennials — stuck at home during the pandemic. Mack and Kayla are inclined to eat as much internet delivery food as humanly possible, and live to tell you about it. They’ll give you no-bullshit ratings of the city’s most eclectic cuisines from the DoorDash app, so you know what to order next.  


Portillo’s, 100 W. Ontario St., $  

It only seemed right for us to inaugurate DoorDash Diaries with a meal from one of Chicago’s iconic chains: Portillo’s. The fast-food staple can be controversial among Chicagoans. Some insist that the place is overhyped, while others champion it as a godsend.  

With our stomachs running on empty, we ordered a massive Portillo’s haul: meat, fries, milkshake —  the classics. When the meal arrived, we were greeted by a small child, likely employed by his parents to help run orders from car to hungry homes. He seemed to understand the urgency of the matter, quickly handing off the food, snapping a super flattering photo of us for confirmation, and scurrying away to the warmth of his motor vehicle.  

With the scene set and our meals cooling to an appetizing room temperature, we dug in and devoured. Here are our thoughts.  

Mack’s review: Chili cheese dog and polish sausage with cake shake and fries  

It is commonly known that the Portillo’s Midwestern empire began in the humble confides of “The Dog House” — a 6’ x 12’ trailer-turned hot dog stand — created by Dick Portillo and situated on Chicago’s North Avenue. It’s a classic tale of pull-yourself-up-by-your-bootstraps, military-fly-over, red-white-and-blue American Dream of Dicks and hot dogs! Freedom tastes like wieners.  

So what makes the perfect all-American meal? Here’s my indisputable mathematical equation, broken down into three components. 

Sweet: Chicago’s Famous Cake Shake lives up to the hype. Portillo’s expands the realm of human possibility, showing us what civilization is capable of achieving: It’s a cake within a shake, but it’s also a shake within a cake. Drinking chocolate cake is some sweet, smoothing, Inception-type shit. It will make your taste buds gush and your brains explode. 10/10. 

Salty: Crinkle-cut fries often carry a bad rap. They’re a lunchtime afterthought; pre-frozen, made-to-scale plate-fillers, engineered by hacks and gobbled up by hangry patrons at amusement parks and sporting events. Portillo’s imagines a brighter path forward for an oft-disrespected U.S. staple. Portillo’s crinkle-cuts are crunchy on the outside, warm on the inside, and beautifully drenched in salt. It’s a well-rounded fry that carries its weight in gold. 8/10. 

Savory: America runs on MEAT. Any flag-shirt-wearing, amateur grilling BBQ chef will tell you that burgers, steaks and hot dogs are the essential foundation of a very patriotic meal. The Maxwell Street Polish Sausage steps up to the plate, but only does a serviceable job of filling star-level expectations. It’s juicy and chewy, but not anything special. The chili cheese dog was the biggest disappointment of the meal; it was delivered at a lukewarm temperature, and the dog’s texture was far too pillowy, blending into the bun to form one homogenous mass. 5/10.  

Portillo’s has all the necessary components for greatness. But its lack of balance in the savory section — the most essential factor of the equation — drops its score significantly. Dogs just don’t deliver well in our new gig economy.  

Rating: 7.2/10  

Kayla’s review: Chicago combo bowl with cheese fries  

This isn’t my first Portillo’s rodeo, so I decided to venture outside of my regular chicken sandwich and try something different. I ordered the Chicago combo bowl — a new Portillo’s menu item — which consists of juicy Italian beef and sausage, topped with melted cheddar shreds and two sweet peppers. (Side note: The peppers and cheese cost extra, and I probably could have done without them.)  

While the sausage was truly meaty and quite large, it was a bit too much protein for my liking.  It felt like I was chomping into a dense meat stick (graphic, I know), and it oozed with oil. The Italian beef, however, was much tastier. The thinly sliced meat was dripping in gravy, leaving my tummy full. It also had a nice touch of seasoning, but wasn’t too salty, spicy or overpowering. Considering the bowl didn’t have any grains to soak up the juices, the meal held up nicely —  even after a venture in the DoorDash car.  

Both as an appetizer and as a dessert, I chowed down on some salty, lukewarm crinkle-cut french fries and finished them off one by one. The added cheese sauce hit the spot, providing a perfect finishing touch for the fluffy fries. 

Though the sausage was a miss and the Italian beef only slightly above average, the french fries saved the meal. And I’ll give bonus points for the cute 8-year-old who delivered it to me. Not too shabby for a DoorDash meal.   

Rating: 7.4/10  


Kayla Huynh contributed to this story.

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culture, food

Mack Liederman View All

Mack Liederman is Redacted Magazine's content editor. He holds a B.A. in political science from Vassar College, where he also served as Editor-in-Chief of the student newspaper. Currently based in Chicago, Mack is a graduate student specializing in sports media at Northwestern's Medill School of Journalism. Mack has both sophisticated interests and boyish sensibilities.