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The best Cuban sandwiches in Chicago

After sampling our weight in the king of toasted sandwiches, we've narrowed down the best and even crowned a winner.


We could debate forever the history of the Cuban sandwich (some say it’s truly a Cuban invention; others say it first popped up at Cuban-run lunch counters in Florida), and there’s even some discord as to the core formula (the addition of salami is common in some areas but has fallen out of the equation in Chicago). So for the sake of this experiment, that is, sampling a host of Cubanos found locally, let’s go over a few key points. (1) A Cuban sandwich should consist of sliced ham, roasted pork (lechon asado), mustard, pickles and a Swiss-type white cheese on “Cuban” bread that is generally softer and wider than a baguette. (2) Cuban sandwiches should be toasted on a flat-surfaced sandwich press known as a plancha (Spanish for grill). (3) Cubanos average five bucks, are ordered over a counter and are intended to be eaten while standing—all the more reasons they are among the world’s greatest inventions. Now, let’s begin, starting at the bottom and working our way to the best…


Café con Leche (1732 N Milwaukee Ave, 773-486-3101)
Oh, Café con Leche, how do we say this and not sound like a jerk? Well, first, something nice: The dogs on your patio add an adorable Peach Pit vibe to the place. Now, the cold, hard truth: I couldn’t finish your Cuban sandwich. And I am a pig. The mustard was absent and the roasted pork had zero flavor, was incredibly dry and was sliced entirely too thick. But the worst offense? In what must have been a momentary lapse in judgment, you added bologna to your Cubano, permeating every bite with the unmistakable funk of fourth grade.


El Rinconcito Cubano (3238 W Fullerton Ave, 773-489-4440)
Mayo as well as mustard? Fine, even forgivable; but no pickle at all? Chewy roasted pork? Incredibly strange snow-white cheese that would probably outlive us all? No dice.


El Cubanito (2555 N Pulaski Rd, 773-235-2555)
See those boot-clad construction workers popping in and out of that brightly painted shoebox-size building? No, this is not the dump spot for hot miter saws; it’s the home of cheap, fast midday snacks. Kudos to the crunchy crust and the even bread-to-filling ratio, but the unseasoned roasted pork was fairly flavorless and dry—and the sliced pressed ham tasted watery.


Cafeteria Marianao (2246 N Milwaukee Ave, 773-278-4533)
The granddaddy of the area’s Cuban lunch counters ascribes to the no-muss, no-fuss theory, meaning this sandwich is the thinnest, most minimal version around. The roasted pork is well salted but not delicious enough to eat on its own, but that’s not our biggest gripe: Only the tiniest sliver of pickle was found on each half, and not even a whisper of mustard was used. A Cuban without that pickle-mustard tang to balance the rich cheese and salty pig is just a wasted opportunity.


La Unica (1515 W Devon Ave, 773-274-7788)
Mayo haters beware: This place loves the stuff. It’s slathered on the bread and even between the slices of ham. That sin aside, this sandwich has a hefty dose of pickles, incredibly gooey cheese and juicy, tender roasted pork. If you can overlook the mayo, this is a mighty tasty Cubano.


90 Miles Cuban Cafe (3101 N Clybourn Ave, 773-248-2822)
Uhm, wheat bread? A tofu Cubano? Is the griddle guy practicing Bikram yoga? What the hell is going on here? Actually, the disarmingly friendly owners of this newcomer are just looking to accommodate those seeking healthier options. But of course, we went straight for the cheese-and pork-packed original—the thickest of any Cubano we tried. The roasted pork got a bit of griddle time before it was added to the mix, which nicely caramelized the edges of the meat. That pork was sandwiched between two helpings of ham, plenty of cheese and lengthwise strips of pickles sliced thicker than most. Good value but almost too much to manage.


Con Sabor Cubano (2739 W Lawrence Ave, 773-728-2226)
Oof. This was a tough one. Deli slices were swapped out for fantastic thickly sliced country-style ham, and salty, cured jamón serrano popped up out of nowhere, confusing but ultimately wooing me. In fact, I thought we had a winner here, what with the crusty, just-thin-enough bread and nearly perfect meat-to-toppings ratio. But the roasted pork killed the mood, with its slightly dry, somewhat stringy texture. Fix that and you have one hell of a sandwich.


Habana Libre (1440 W Chicago Ave, 312-243-3303)
This dark, little West Town BYOB should teach the military a thing or two about covert operations. It would appear to be a sit-down restaurant specializing in hefty plates of lechon asado and other classics. But that same incredibly tender, marinated, slow-roasted pork can also be piled onto garlic bread between slices of sugar-and-salt-cured country-style ham with pickle, Swiss cheese and mustard for an elevated take on the Cuban. The only thing that kept it from winning was the undertoasted, soft and poofy bread slathered with distracting garlic butter.



Cafecito (26 E Congress Pkwy, 312-922-2233)
After swooning over the first Cubano I tried from this new café adjacent to Hostelling International, I thought perhaps I was swayed by the parade of young, thrifty, foreign hotties lounging about. So I took the next sandwich to go, lest I be influenced by other factors. Turns out, it’s still delicious, and the key to its success is the citrus-garlic-marinated, cumin-rubbed lechon asado and the perfect toasting (whoever is operating the plancha needs a raise).

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