I ordered the same meal at Freddy's and Portillo's. As a Chicago local, I was shocked by the winning restaurant.

I ordered the same meal, including a chili cheese dog, chicken tenders, and a milkshake, at Freddy's and Portillo's to see which had the best food.

Apr 22, 2025 - 18:24
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I ordered the same meal at Freddy's and Portillo's. As a Chicago local, I was shocked by the winning restaurant.
The author's meal at Portillo's; a vanilla milkshake, chili cheese dog, and chicken tenders.
The chili cheese dog at Portillo's had different toppings than the one at Freddy's.
  • I ordered the same meal at Freddy's and Portillo's to see which one was best.
  • I was pleasantly surprised by the toasted bread Freddy's used for its chili cheese dog.
  • Portillo's vanilla milkshake tasted like a thicker version of soft serve ice cream.

As a Chicago native, I'm very familiar with Portillo's. The fast casual restaurant chain serves a variety of my city's hallmark foods, including Italian beef sandwiches, Chicago-style hot dogs, and my usual go-to order, a Maxwell Street Polish sausage.

I wasn't as familiar with Freddy's Frozen Custard & Steakburgers, another popular fast-food chain with locations across the US, but when I heard great things about their food, I decided to give it a try to see how it compared to Portillo's.

I ordered the same meal — a chili cheese dog, chicken tenders, and a vanilla milkshake — at both. Here's how the restaurants compared.

Prices may vary by location.

I visited Freddy's first.
The interior of a Freddy's, complete with bright red tables, booths, and chairs. There's also a sign in cursive that says,
Freddy's Frozen Custard & Steakburgers has more than 500 locations in the US.

Freddy's was founded in 2002 and has since grown to have more than 500 locations across the US.

My partner and I were the only customers when we arrived on a Sunday at 11 a.m. We were greeted by bright pops of red and a 1950s diner aesthetic that still felt modern.

I paid $7.30 for my chili cheese dog, $8.30 for a large order of chicken tenders, and $5.20 for a regular vanilla milkshake, bringing my total to about $22 including tax.

Freddy's chili cheese dog is a must-try menu item.
The author's chili cheese dog, chicken tenders, and vanilla milkshake from Freddy's.
I loved the bread used for Freddy's chili cheese dog.

I had no expectations going into Freddy's, and it didn't take long to receive my chili cheese dog and chicken tenders.

With a significant amount of chili, thin shreds of cheese, and diced onions, I was pleasantly surprised by my meal as soon as I saw it.

The bread was something special and reminded me of Texas Toast, with just enough sturdiness to hold this notoriously messy dish together. Plus, it didn't get soggy even after sitting for a while. The toppings barely spilled as I ate, and the hot dog was grilled to perfection and tasted great.

Meanwhile, the chicken tenders were on the thinner side. They weren't overly breaded, but tasted well-seasoned and crispy.

The vanilla milkshake was made with Freddy's signature frozen custard and was very thick, but easy to drink with the size of the straw provided.

Then, I went to Portillo's.
The interior of Portillo's, with road signs like,
Portillo's is a smaller chain than Freddy's.

Portillo's was founded by Dick Portillo in 1963 as a hot dog stand called "The Dog House," and has since grown to have more than 70 locations in the US.

Walking into Portillo's was familiar territory. The location I visited had an interior theme that drew from the 1920s and the Great Depression.

I placed my order at a self-service screen and waited to hear my number called.

I paid $5.50 for my chili cheese dog, $6.20 for four chicken tenders, and $5.30 for a large vanilla milkshake, bringing my total to about $19 including tax.

Portillo's chili cheese dog tasted good, but the chicken tenders were disappointing.
The author's meal at Portillo's; a vanilla milkshake, chili cheese dog, and chicken tenders.
The chili cheese dog at Portillo's had different toppings than the one at Freddy's.

I was underwhelmed after opening my chili dog. The chili was more saucy, with little meat or beans, and there wasn't much of it. There was, however, a decent layer of nacho cheese underneath.

Portillo's uses poppy seed buns for their chili cheese dogs, and although this is a delicious option, I don't think it provides the support this dish needs. Although the bread didn't break, things got messy and it became more of a hassle to eat than Freddy's option.

Still, the best part of the chili cheese dog was the hot dog itself. Portillo's uses Vienna Beef products, the signature sausage for a Chicago-style hot dog. Together, the Vienna Beef hot dog and poppy seed bun made the chili dog worth the extra mess.

The chicken tenders tasted good, too, but overall, I was disappointed by them. The breading was thick and had a nice crunch in some spots, but left little to no chicken in other bites.

Since the tenders were fried fresh, I ripped them in half to allow each to cool faster, but in doing so, the breading started to slide off, leaving me with naked pieces of white meat.

Finally, I ordered a large milkshake because Portillo's didn't have a medium option. My shake came in a huge cup and was $0.10 less than the medium I received at Freddy's. It tasted like I was drinking a thicker version of soft serve vanilla ice cream.

Now, I understand the hype around Freddy's.
The author sitting in a booth at Freddy's, smiling.
I enjoyed my experience at Freddy's, but will always love Portillo's.

I now fully understand the hype around Freddy's. The quality of the food is fresh and tasty, and I think you get a better experience here for about the same price as other fast-food restaurants.

However, this review doesn't eliminate Portillo's from my rotation. Some of the items I typically order can only be found at Portillo's and other local Chicago spots, so although Freddy's won this competition, there are other ways it just can't compare.

Read the original article on Business Insider