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You never have to travel far to find some Caribbean food on the South Side. However, most options from the islands will be Jamaican. One of the exceptions is Cafe Trinidad, which recently moved into new digs on 47th Street in Bronzeville. They're the first and, to my knowledge, still the only restaurant in all of Chicagoland specializing in the food from Trinidad and Tobago. The two island country is one of the oldest inhabited areas of the Caribbean, so it's cuisine is influenced by many flavors, including those from Africa, India, China, Britain, and others.
One of the best ways to taste all those flavors together is in a roti, which one might describe as a burrito from the islands. However, its roots go back to India where stoneground wholemeal flour is used to make a thin flatbread. It's now considered one of a few national dishes from Trinidad and Tobago, and over time they've built their own style of the dish, so the way it's made there can vary.
At Cafe Trinidad they make a Dhalpuri style version, which takes ground yellow chickpeas, toasted cumin, garlic, and pepper and turns that into a filling that is pushed into the dough and sealed. When rolled, the filling is distributed within the roti. It then gets rubbed with oil and cooked over a flattop specifically made for toasting them.
When you're feeling like a roti, it's not just some of the bread, but also a combination of curried meats and vegetables or a stew thrown in it and wrapped. Fillings include typical Caribbean staples like jerk chicken (boneless or bone-in), goat, oxtail, shrimp, and veggie-based options like callaloo. Whichever you choose, it will include curried potatoes and chickpeas and will come with a scorching hot yellow scotch bonnet sauce on the side.
If you do go boneless you could make an attempt at eating it like a burrito, however you should know that some meats include bones. While you could also attempt to eat around them like a Maxwell street pork chop sandwich, I suggest opening it up and using the roti as your utensil. I just remove the meat from the bones.
This trip I enjoyed the tender and subtly flavored goat, scooping it up with ripped pieces of roti. Much like the Carnival celebration the island is known for, it has a lot of tang going on. I'll always appreciate Cafe Trinidad because they introduced me to a style of food I can seek out when traveling in areas where it's more readily available (Toronto and South Florida). I'd also like to travel to the islands one day. I suspect the eating would be awesome. Get your doubles fix on Saturdays. It's all good man.