Sergio Di Sapio's father Rodolfo started selling empanadas on Southport in 1981. Photo: Janet Rausa Fuller

A proper empanada crawl takes roughly 514 steps—fewer if you're hungry—along a two-block stretch of Southport Avenue between Addison and Grace.

Call it Chicago's unofficial empanada district or, as one local business owner says, Argentine Alley, marked on the north by El Mercado Food Mart (3767 N. Southport Ave.), on the south by Cafe Tola (3612 N. Southport Ave.), and in the middle by 5411 Empanadas (3715 N. Southport Ave.), each of which sells empanadas by the hundreds daily.

To complete the Latin-themed meal, Frío Gelato (3721 N. Southport Ave.), which opened in April, scoops Argentine gelato as smooth as the Italian stuff in flavors like dulce de leche, malbec, and yerba mate. 

It should be noted that Cafe Tola specializes in Mexican-American, not Argentine, empanadas. Nevertheless, this Lakeview strip is as good as any to take in three distinct styles of the popular pastry.

The empanada's prominence on Southport can be traced to El Mercado, which offers traditional versions such as ham and cheese and sweet corn in a heated case at the front counter. Rodolfo Di Sapio, a butcher and Argentine immigrant, started cutting meat at the corner store in 1976. Four years later, he bought the place from his Cuban boss, bulked up the shelves with goods from Argentina, and began making and selling beef and chicken empanadas, according to his son and current owner, Sergio Di Sapio. The elder Di Sapio died in 2014.

Back then, the middle-class, mixed-race neighborhood was "just kind of dead, businesswise," says Sergio, 42, who attended Blaine Elementary across the street and learned as a boy how to crimp the empanadas by hand. The Di Sapios became known within Chicago's Argentine community as the go-to source for a taste of home, be it cut-to-order steaks, chewy dulce de leche-filled alfajores, or those warm empanadas—even more so when Sergio opened Tango Sur, a steakhouse, next door in 1996. (Pro tip: You'll find the most variety at El Mercado.)

Sleepy storefronts eventually gave way to trendy boutiques and gleaming condos. Sergio admits he and his father watched with some consternation in recent years as the meat-pie options on the street multiplied. "At first I was like, 'What the hell? Everybody's coming over here.' But then I thought about it and was like, 'Whatever. People will taste and see which one they want,’ " says Di Sapio.

Even his competitors, who shy away from that term, count themselves as customers and friends. "Tango Sur is the one Argentine steakhouse that everybody knows and goes to. We love them," says 5411’s co-owner Nicolas Ibarzabal, who has played on Tango Sur's recreational league soccer team. Ibarzabal opened the Southport shop, 5411’s fifth, in June 2016 with three fellow Argentines. The busy corridor had always been in their sights as an ideal spot. Being near Di Sapio’s businesses hasn’t hurt. “We’re all very different,” he says.

Likewise, Victoria Salamanca didn't intend to step on any toes when she converted the tiny building that had been her husband's extermination business into Cafe Tola in 2012 and began selling coffee and empanadas inspired by her grandmother's cooking. "It was something that was popular on my catering menu that would be easy to put in people's hands," says Salamanca. "At first I remember [Rodolfo Di Sapio] being upset, like, who were we to make empanadas?" 

Any hard feelings have since dissipated. "They gave us the blessing. We're good friends," she says with a laugh. "I feel so grateful to be in the neighborhood."

"It's fine. It's all good,” Sergio Di Sapio says. “My cousin jokes that since they opened the other empanada places, we're busier. I don't know what that means.” 

Ibarzabal has a theory: "I'm a big believer that the more empanadas, the better for everybody. I think they're still a product that needs to be out there more.”

Sales are healthy for their newest neighbor, too. “It’s synergistic for all of us,” says Karla Tennies Koziura, who owns Frío Gelato with husband Sebastian Koziura, an Argentine native.

Last December, Di Sapio expanded again with Bodega Sur (3755 N. Southport Ave.), a wine and tapas bar. Cafe Tola is growing as well. Dona Tola, a sit-down, Mexican comfort-food restaurant under construction, is a mere two doors south of Bodega Sur. It will function as a commissary kitchen, supplying the empanada fillings for all of Salamanca’s locations. 

But, out of deference to her neighbors to the north, Salamanca says she’s leaving empanadas entirely off the menu.


Empanadas Aplenty: A Comparison

Empanadas from Cafe Tola (left), El Mercado (front and center), 5411 Empanadas (right)Photo: Janet Rausa Fuller

There are obvious differences between the empanadas at El Mercado, 5411 Empanadas, and Cafe Tola. Cafe Tola's are the largest. El Mercado's are the cheapest. 5411's are baked, not fried. Here's how else they stack up.

El Mercado

Variety: Fried and baked, 10 to 12 fillings.
Price: $1.50 to $1.99
Philosophy: "We cut our meat fresh every day, no waste. We don't use cheap meat. We use a different dough for the baked ones that's very flaky. It's a secret."
One to try: Sweet beef with olives and hard-boiled egg.

5411 Empanadas

Variety: Baked, 15 fillings.
Price: $2.75
Philosophy: "Our dough is thinner. We don't want you to fill up on dough or bread. We want the filling to be the most important part of the empanada."
One to try: Bacon, dates, and goat cheese. 

Cafe Tola

Variety: Fried, 31 fillings, 12 typically in rotation at a time.
Price: $4.25
Philosophy: "Ours are influenced by guisados, the homestyle foods I grew up eating. My father always said, 'If you're going to cook food, make sure to give them their money's worth.' "
One to try: Green spicy pork with cactus and black beans.