I tried one of the most famous hot dogs in Chicago and it was delicious -- but I made one huge mistake while ordering

Sarah Jacobs/Business InsiderChicago hot dogs are serious business. But bigger isn’t always better.
  • Hot dogs in Chicago are a big deal.
  • Portillo’s is a fast-casual restaurant that’s located throughout Illinois and serves a classic Chicago-style hot dog.
  • Chicago is famous for its hot dog, which is an all-beef Vienna dog topped with mustard, neon-green relish, tomatoes, white onions, a pickle spear, sport peppers, and a shake of celery salt.
  • The perfect Chicago hot dog needs to have ‘OBR’ – the optimal bite ratio of toppings – according to Chicago food expertSteve Dolinsky.

The hot dog has historical significance in the city of Chicago. The all-beef Vienna dogs with the essential seven toppings nestled in a poppy-seed bun is a thing of culinary legend.

Even the award-winning, Michelin-star chef Grant Achez of Alinea – one of the best restaurants in America – tips his hat to his city’s most classic food.

Portillo’s, a chain resturant with a majority of its 53 locations scattered throughout Illinois, serves among other things, a classic Chicago-style dog.

Portillo’s started as a simple hot dog stand in 1963. Known as “The Dog House,” owner and founder Dick Portillo invested $US1,100 into the business – only to grow his empire and reportedly sell it for nearly $US1 billion in 2014 to Berkshire Partners.

While in town for the James Beard Awards this month, I stopped at Portillo’s to see what all the fuss is about.

It’s obvious the people of Chicago love Portillo’s.

In 2014, right after the company was sold, The Chicago Tribune reported that the newer Portillo’s locations brought in an average of $US7 to $US8 million annually. In 2018, at around 11:30am on a Monday, I expected the Portillo’s on W. Taylor Street near down town Chicago to be mostly empty – but upon walking in, I found diners already wrapping up their finished meals and heading out for the rest of their work day.

I tried my first ever Chicago hot dog, and chatted about my experience with Chicago food expert and tour guide, Steve Dolinsky, whose insight into the city’s favourite and most historic dish helped me appreciate it even more.


I went to the Portillo’s located at 520 W. Taylor Street. Like their other locations, this Portillo’s serves a variety of foods including ribs, burgers, chicken sandwiches, salads, and more — but my plan was to eat the only menu item that matters: the hot dog.


Each Portillo’s location is decked out in the theme of a different decade. This particular location is 1930s themed.


Portillo’s hot dog menu options are straight forward. You’re either ordering a classic Chicago style hot dog (regular or jumbo-sized), a chilli cheese dog, or a Polish style dog.


Here’s the only mistake I made: I ordered the jumbo-style Chicago hot dog. As a native Texan, I’ve been conditioned to think that everything that’s bigger is better. But apparently in Chicago that’s not the case.


As Dolinsky so eloquently put it, my “OBR,” or optimal bite ratio, was messed up because I went with the larger dog.


As a less experienced hot dog consumer, I’m used to three condiments: ketchup, mustard, and relish. So, as I witnessed this Portillo hot dog master craft my Chicago style dog, my mind was blown.


Most importantly, there’s no ketchup involved. “Ketchup never goes on a hot dog,” said Dolinsky. “Because, first of all, it’s crap. It’s too sweet. You want that mustard to cut through that beefiness.”


The “seven holy condiments” as Dolinsky calls them are: yellow mustard, neon-green relish, sliced tomatoes, chopped white onions, a pickle spear, sport peppers, and a shake of celery salt. To make it a Chicago dog, these toppings along with an all-beef dog, must be served in a steamed poppy seed bun.


Down to the last shake of celery salt, Portillo’s delivers on these tried and true ingredients.


My first bite into the dog was a spicy one — which was a confusing experience since I’ve never associated hot dogs with that kind of heat. The sport peppers gave it this kick.


Dolinsky was right — you can’t order a jumbo style dog in Chicago. The size messed with the ratio between the hot dog and the pickle. The consistency was confusing because everything else was relatively easy to chew and soft, and then you had this pickle spear that was difficult to bite into.


The sesame seed bun was super soft and delicious, but didn’t hold together too well. At this point in the meal I was glad the only liquid condiment on this hot dog was mustard — ketchup would have completely destroyed it.


Overall the amount of flavours within this one simple dish was overwhelming in a good way. The onion, sport peppers, and the pickle particularly stood out flavour-wise — and for someone who is used to relish being the only green condiment on a hot dog, this opened up my world to new and delightful possibilities.


While Portillo’s isn’t Dolinsky’s favourite hot dog spot (he prefers Super Dawg) he noted that they certainly make a “a pretty respectable Chicago dog.” I agree.

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