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Preheat your oven to 375°F (190°C).
Cut off the tops of the bell peppers, remove the seeds, and discard. Place the peppers upright in a baking dish or on a lined baking sheet.
In a large skillet, heat a bit of oil over medium heat. Add the diced onion and minced garlic, and sauté until translucent and fragrant, about 2-3 minutes.
Add the shredded chicken, diced pineapple, cumin, paprika, dried oregano, salt, and pepper to the skillet. Mix well and cook for an additional 2-3 minutes to allow the flavors to meld together.
Spoon the chicken and pineapple mixture evenly into the bell peppers, packing it tightly. If desired, you can also add a small amount of cooked rice or quinoa to fill any remaining space inside the peppers.
Place the stuffed bell peppers in the preheated oven and bake for 30-35 minutes, or until the peppers are tender and lightly browned.
Remove from the oven and let them cool for a few minutes before serving. Enjoy your delicious Cuban-style chicken and pineapple stuffed bell peppers!