Chicago may not have a huge Cuban food scene, but what we do have is more than worth checking out. We love the Cuban sandwich at Cafecito, the guava and cream cheese pastry at 90 Miles Cuban Cafe, the pan con timba at Cubano, the roast pork dinner at La Unica and the rum cocktails and ropa vieja at Paladar. Here's where we go when we're in the mood for a Cuban restaurant.
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Chicago Cuban restaurant guide
Blink, and you might miss this cigar-box-size Cuban carryout spot tucked away off a dusty strip of Clybourn Avenue. That would be a shame, especially if you’re looking for a morning pick-me-up. Potent café con leche and cortaditos are the perfect pair with guava and cream cheese pastries, best enjoyed at one of the counter stools while waiting on a lunch order for later. A second location makes getting the meaty Cuban sandwich or the guajirito, essentially a Puerto Rican jibarito that piles marinated nickel-thin steak, grilled onions and cheese onto crispy green plantains, even easier.
You don’t have to claim a bunk at the adjacent Hostel International to get your hands on one of this café’s ridiculously good Cuban sandwiches. Sure, sides of roasted eggplant salad and jalapeño hummus are flavorful, but there’s no confusion over the star of the show: the Cubano’s crusty bread is toasted just right, its roast pork juicy, its pickles thick, and its mustard and gooey cheese plentiful. And once it’s devoured, only a potent café con leche will keep you from calling the café’s comfy couch home for the day.
It seems counterintuitive, but trust us: You’re going to want to eat a sandwich as your entrée and then get a second sandwich for dessert. Start with one of the Cubanos—the crusty bread grilled to a flaky crunch, the pork and ham complemented by a healthy slathering of mustard—and wash it down with a coconut soda. But don’t fill up: If you don’t order the pan con timba—warm bread, mild slices of Swiss and a sweet center of guava—you’re missing the best part.
Wind through the aisles of this “food mart” to the rear corner and you’ll find a dozen tables, a friendly counterman and a wall lined with brightly colored signs touting house specialties. (Grab an English menu from the counter if your Spanish is weak.) The Cuban sandwich is among the best in town; pork-filled tamales, crunchy bacalao (salt cod), the roasted pork dinner with yellow rice and garlicky green and caramelized sweet plantains are all must-haves, too. Top off the meal with a round of the perfectly rich and slightly sweet café con leche.
It makes sense that Jose Gonzalez named his restaurant after Cuban paladares (private restaurants often run out of people’s homes): This Logan Square spot has a surplus of warmth and homeyness. The sign outside calls Paladar a rum bar, and you’d do well to start your meal with the “premium” mojito, which has a deeper, more distinctive flavor from fresh sugarcane juice. But though there’s a designated bar area up front, Paladar is more an easy, quiet restaurant, where standard appetizers (empanadas, tamales) make way for standout main courses, like rich, comforting ropa vieja accompanied by sweet plantains and tender rice.