In a bowl, coat the chicken breasts with jerk seasoning and drizzle with olive oil. Massage the spices into the chicken. Let it marinate for at least 30 minutes (or up to 4 hours in the refrigerator for enhanced flavor).
Preheat a grill or stovetop grill pan over medium-high heat. Cook the marinated chicken for about 6-7 minutes on each side, or until fully cooked and juices run clear. Let it rest for a few minutes before slicing it into thin strips.
In a separate bowl, toss together the diced pineapple, shredded red cabbage, sliced red onion, and chopped cilantro. Drizzle with lime juice and sprinkle with a pinch of salt. Mix until well combined.
Briefly warm the tortillas on a skillet or grill for about 30 seconds on each side, until they become pliable.
On each tortilla, add a few strips of jerk chicken, followed by a generous portion of the pineapple slaw. If desired, top with sliced jalapeños for extra heat.
Enjoy the tacos immediately, garnishing with more cilantro or a lime wedge on the side for added flavor.