Peel and core pineapple. Cut the pineapple flesh into planks about 1 inch thick and 3 inches long to yield about 2 cups. Place the sliced pineapple, oil and 1 tablespoon adobo in a medium bowl; toss until combined.

Finely chop more pineapple to yield about ¼ cup. Transfer the chopped pineapple to a large bowl along with any accumulated juices. (Reserve remaining pineapple for another use.)

Finely chop 2 to 3 chipotles to yield roughly 2 tablespoons; add to the large bowl with the chopped pineapple. Whisk in honey and ¼ cup adobo. (Reserve remaining chipotles and adobo for another use.) Add chicken; toss to coat. Cover and let stand at room temperature for 15 minutes.

Preheat grill to high (450°F to 500°F). Remove the pineapple planks from the marinade; place on oiled grates (reserve remaining marinade). Grill, uncovered, turning once, until charred and tender, 2 to 3 minutes per side. Transfer to a large platter.

Remove the chicken from the marinade; sprinkle with ¾ teaspoon salt (discard chicken marinade). Grill the chicken on oiled grates, uncovered and turning once, until the outside is caramelized and an instant-read thermometer inserted into the thickest portion registers 165°F, 6 to 8 minutes per side. Brush the tops of the breasts with the reserved pineapple marinade; grill for 1 minute more. Transfer to the platter with the pineapple.

Serve the chicken breasts whole or sliced with the grilled pineapple and fresh avocado. Season everything evenly with remaining ¼ teaspoon salt before serving.