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From giant platters of Dominican food sided with sweet plantains to jibaritos to an astounding two pounds of jerk chicken wings, the eating is good, the easy breezy atmosphere even better.
Maxine's Caribbean Spice
1225 E. 87th St.
Chicago, IL
60619
(773) 933-0540
Hours: lunch and dinner daily; breakfast Saturday-Sunday
You can't order grilled cheese and chocolate malt at this diner, which dishes up plenty of – you guessed it – Caribbean spice. Its jerk chicken gets the loudest raves, but it shares menu real estate with plenty more winners: curried goat, oxtails and beans, and Jamaican pineapple chicken. If you're willing to pay a little more than diner prices, try the curried lobster or red snapper. The service tends to be a little slow, but the food is worth the wait. Weekends pack in even more diners hankering for a Caribbean-style breakfast of beef kidney, liver and onions, fried dumplings, and boiled bananas.
Tropic Island Jerk Chicken
419 E. 79th St.
Chicago, IL
60619
(773) 224-7766
Hours: lunch and dinner daily
The location leaves a little to be desired for some, but few will disagree that the jerk chicken is worth the trek. Sauce is served on the side, meaning you can douse your meal in hot-and-spicy jerk delightfulness or go light on the good stuff. The jerk chicken is the big draw, and is served a boatload of ways: whole, half and quarter chicken, white or mixed meat; jerk wings; and Jerk-E-Que wings served with Jamaican dough bread. You'll also find jerk catfish, curry shrimp and goat, oxtails and more, served with red beans and rice and your choice of two sides.
Cafe Trinidad
555 E. 75th St.
Chicago, IL
60619
(773) 846-8092 http://www.cafetrinidad.com Hours: lunch and dinner Tuesday-Sunday
Whether you choose the curry goat, oxtail stew, fried chicken wings or Trini perch, expect to get a giant platter of eats that hail from Trinidad and Tobago for just under $10. Your meal comes served with rice and peas, a slice of roti (a soft, flat bread filled with ground yellow split peas and spices) and your choice of side, from a long list that includes Trini-style macaroni pie, plantains and callaloo, a creamy combo of spinach and okra. If you're into fish and spice, try the curry salmon or curry crab legs and dumplings, a nice change from the shrimp and tilapia norm.
As you might guess from the name, it's not unusual to hear a steady stream of steel drum music at this Jamaican haven in Hyde Park, which lets you do as you would were you on the island: eat and drink with wild abandon. Its famous jerk wing appetizers come in a whopping two-pound portion for $10, though it's only one dish on a massive menu that include conch fritters, plantain nachos, grilled mahi-mahi and smoked jerked baby back ribs. Whatever you order, pair it with a rum- and amaretto-based Bahama Mama and a slice of key lime pie.
Nathan's Chicago Style
1372 E. 53rd St.
Chicago, IL
60615
(773) 288-5353
Hours: lunch and dinner daily
If you're inclined to think that Nathan's sounds a little more like a hot dog stand than a Caribbean wonder, you're right ... almost. This Hyde Park spot doesn't have the dine-in charm of Calypso Cafe, but if you're looking for a jerk-flavored bite on the fly (and are with a friend whose sense of adventure doesn't extend beyond the bacon cheeseburger), this is your spot. In addition to Philly cheese steaks and Polish sausages, you'll find jerk and curried chicken, curried goat with rice and peas, fried plantains and homemade ginger beer.
Cafe Bolero
2252 N. Western Ave.
Chicago, IL
60647
(773) 227-9000 http://www.cafebolero.net Hours: lunch and dinner daily
This classy Cuban restaurant is a bright spot along an otherwise middle-of-the-road stretch of Western Avenue. Exposed brick, white tablecloths and a glowing red bar in the rear make it utterly date-worthy, but where the tab ends up is entirely up to you. Keep it casual by grabbing a seat at the front counter, which sits directly in front of the grills, and watch the chefs whip up your $5 cubano. If you're looking to impress, get cozy over a $45 order of paella for two. Or take the tapas route: You can’t go wrong with Bolero's pulpo con ajo, octopus sauteed with garlic and oil.
Cafeteria Marianao
2246 N. Milwaukee Ave.
Chicago, IL
60647
(773) 278-4533 http://www.centerstagechicago.com Hours: breakfast and lunch daily
Praised by the foodies at LTHForum, this shack of an eatery does a good job of proving the don't-judge-a-book-by-its-cover adage. Elbow your way up to the counter, speak the best Spanish you can and order a cubano; ham, egg and cheese sandwich; or steak sandwich from one of the cooks hustling in front of you. The French bread is perfectly crusty, the cafe con leche is nice and creamy, and your tab for two sandwiches (heck, throw in a churro) won't top $7. There are a few stools along the window-side counter, but it's a stand-and-eat spot otherwise.
The Winds Cafe dishes up "American cuisine with a Caribbean flavor" in a bar-&-grill atmosphere that's totally comfortable. An all-you-can-eat Sunday brunch mixes all those USA breakfast faves (French toast, eggs, biscuits and gravy) with jerk chicken, catfish nuggets and irresistible Absolut Peppar bloody marys. Open until 2 a.m. most days, you'll also find Caribbean plates like chuletas, fried seasoned pork chops, and jibaritos sandwiches on its menu. The Winds offers a "jerk of a special" until 5 p.m. every day except Sunday: a mini jerk burger with a Red Stripe for $5.
Doctor C's Caribbean Cuisine
10226 S. Halsted. St.
Chicago, IL
60628
(773) 779-8000
Hours: lunch and dinner Tuesday-Sunday
You needn't dread a visit to this doctor, who operates a bustling pharmacy of spicy goodness. It's a mostly take-out operation, which gives you the green light to order twice the number of dishes than what you'd normally be comfortable eating in one sitting in public. Load up on jerk chicken and catfish, red beans and rice, oxtail, curried goat, and stewed chicken and you'll soon agree that whether the C stands for chef, Caribbean, cook, curry or cuisine, it has to stand for can't-keep-the-crowds-away.
This way-North-Side spot offers a pretty unique menu for the Vitamin C-deprived: Jamaican-style juices. Good To Go's juice bar squeezes out fresh carrot with lime and ginger and homemade Jamaican fruit punch, among others. Match your meal to your appetite: Dinners like jerk pork, brown stew chicken, curry goat, and tripe and beans come in small or large portions, each sided with rice and peas, plantains and steamed vegetables. Check out curry conch and coconut shrimp on the seafood menu, and cap things off with a slice of Jamaican rum cake. Plantain porridge is available on weekend mornings.
Borinquen Restaurant
1720 N. California Ave.
Chicago, IL
60647
(773) 227-6038 http://www.borinquenjibaro.com Hours: lunch and dinner daily
This Puerto Rican restaurant's menu is a long one, but don't expect to spend much time exploring its depths. That's because this "Home of the Jibarito" sells eponymous sandwiches so good that you'll find it hard to order anything but. Get your choice of steak, roasted pork, chicken, ham or vegetarian greens sandwiched between two flattened plantains that stand in for bread. You'll also find fried meat pies, codfish patties, roasted pork, octopus salad and Puerto Rican stew on Saturdays and Sundays only.
This lovely BYOB opened relatively recently, but it didn't waste any time in reaching buzz-worthy status. While the interior is somewhat simple, it serves up a satisfying amount of Cuban charm and low lighting. The menu comes divided into sandwiches, chicken, beef, pork and seafood sections, but you’ll do fine if you never stray from the mariscos part. If you can, order the superb and giant avocado-topped ceviche (available only on weekends) and the snapper. The pork dishes come highly recommended, too.
Punta Cana
1024 N. Ashland Ave.
Chicago, IL
60622
(773) 252-7200
Hours: open daily
This Dominican BYOB may be light on the frills, but it comes heavy on the good eats. Plantain lovers should start with the tostones, oval, silver dollar-size pancakes of mashed goodness drizzled with a potent garlic sauce. Between those and the complimentary chips and salsa, you're likely to be stuffed by the time the main course rolls out. But it'll be hard to resist plowing through the camaroes al mojo de ajo, a half-dozen sauteed jumbo shrimp dripping in garlic oil and sided by sweet plantains, beans and rice and a dollop of guacamole.
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From giant platters of Dominican food sided with sweet plantains to jibaritos to an astounding two pounds of jerk chicken wings, the eating is good, the easy breezy atmosphere even better.
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