#1 Hot Dog ($2.45)
Since Portillo's uses a natural casing dog from Vienna Beef, you're virtually guaranteed a very good hot dog. Still, even of you're expecting greatness, you'll be surprised. That's because Vienna Beef uses a special blend for Portillo's. The differences are slight, but the dog seems to have a more prominent snap, which helps it stand out even more amongst the toppings. As for the toppings, they are fresh and carefully assembled. Add to that soft and steamed bun, and you have one of the best Chicago-style hot dogs in the whole city.
#2 Italian Beef ($4.85)
Portillo's won our Italian beef tasting a few years ago, and while I personally prefer the offering at the original Al's #1 on Taylor, I totally understand how it came out on top. Exceptionally beefy and tender, drenched in gravy, and spiked with some of the best giardiniera in town, this is a sandwich everyone has to respect.
#3 Chocolate Cake Shake ($1.95, small)
Portillo's chocolate cake is kind of a thing, but though surprisingly good, it's one of those things where you take a few bites, admire it, and then set it aside. On the other hand, the chocolate cake shake, which mixes hunks of the cake into a chocolate shake, is so good you'll finish the whole thing before you even realize it.
#4 Grilled Tuna Sandwich ($4.99)
I have to thank former Serious Eats writer and current Chicago Sun-Times dining critic, Michael Nagrant, for this one. Instead of a standard tuna salad sandwich, Portillo's uses a tuna fillet, which is grilled so it picks up some nice charred flavor. The sandwich absolutely trounces the fried halibut fillet, which is just a step above a Filet-O-Fish. (If you want one of those, a massive two-story McDonald's is across the street.)
#5 Char-Grilled Maxwell Street Style Polish ($3.59)
This was a surprise. Too often Polish sausages are dry and crumbly, but not here. Portillo's version is juicy and nicely charred—a truly hard balance to strike. I also love the sweet caramelized onions, which are mere moments away from breaking down into an onion soup. All you need with this guy is a little mustard.
#6 Beef-N-Cheddar Croissant ($4.99)
If you ever thought the Italian beef wasn't ridiculous enough, just add gooey cheddar and replace the roll with a mammoth croissant. But thanks to the spicy giardiniera, which helps cut through the excess here, it doesn't taste like the total grease bomb it may look like. In fact, that ridiculously over-sized croissant might not actually have any of the characteristics that one would associate with a croissant, but it is pillowy soft, and when all the all elements are combined, you're left with a bite that is beefy, cheesy, spicy, crunchy, and creamy. No one should know how many calories are involved in this creation, but all said, it makes Arby's own beef and cheddar look like a chump.
Other Good Options
I sampled a good portion of the menu, and while these aren't the best, these next two items do prove that Portillo's is operating a very high standard. I may have been floored by the chocolate cake shake, but it is easy to see why the chocolate cake ($2.25) is so beloved. Tender and moist without being overly sweet, it's a solid rendition. It's not quite as addictive as the shake, but if you happen to have a soft spot for cake, this is a good choice.
Other Good Options
By design, grilled chicken sandwiches aren't exactly the most exciting option, and too often they are sabotaged by dry chicken meat. But Portillo's Char-Broiled Chicken Sandwich ($4.59) is surprisingly juicy, and balanced by crisp lettuce and loads of mayonnaise. I doubt I'd ever order this again, but, once again, if you have a particular fondness for the sandwich, this is definitely worth it.
Is there anything else I missed? What do you like to order at Portillo's?