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In a food processor, combine diced pineapple, chipotle peppers, adobo sauce, honey, garlic cloves, lime juice, cilantro, and a pinch of salt and pepper. Blend on high until smooth. Set aside for later use.
Season both sides of the chicken cutlets with salt and pepper. Drizzle some olive oil over the cutlets and cook them on your Blackstone over medium-high heat for 3-4 minutes on the first side. Flip the chicken and brush the pineapple chipotle mixture over the cooked side as the other side continues to cook.
If desired, flip the chicken again and baste with the pineapple chipotle glaze once more. Be cautious not to burn the glaze, so flip the chicken often.
Lightly toast the potato rolls.
To assemble the sandwiches, place shredded lettuce, tomato slices, and red onion slices on the bottom half of each potato roll. Top with a fully cooked and glazed chicken cutlet. Serve the sandwiches while hot.
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