Grilled Chicken Pineapple Stacks

There's something about grilling pineapple that stops people mid-conversation. My neighbor called over the fence one summer afternoon, drawn by that caramelized sweetness mixed with smoky char, and suddenly we were talking about tropical flavors on chicken instead of the usual weekend small talk. That's when this burger stack was born—not from a cookbook, but from standing at the grill with a handful of ingredients and the kind of improvisation that happens when good weather and good timing collide.

I made these for a small gathering last summer, and my sister—who usually picks around food—stacked three high before anyone else grabbed a plate. She loved that she could control every layer, adding extra avocado or holding back on the onion. That's when I realized this wasn't really about perfecting a burger; it was about giving people permission to build something exactly the way they wanted it.

Ingredients

• Boneless, skinless chicken breasts (4): Pound them gently to an even thickness so they cook at the same speed and stay juicy inside—nobody likes a dry grilled chicken breast.
• Olive oil (2 tablespoons): The fat carries flavor into the chicken and helps prevent sticking on the grill.
• Soy sauce (2 tablespoons, gluten-free if needed): This is your umami anchor, deepening the marinade without salt alone doing all the work.
• Honey (1 tablespoon): Sweetness that caramelizes on the grill, creating those gorgeous golden marks.
• Smoked paprika (1 teaspoon): Adds depth and a whisper of smokiness even before the grill gets involved.
• Garlic clove, minced (1): Fresh garlic brings brightness that bottled won't match.
• Salt and black pepper: Don't skip seasoning the marinade—this is where flavor starts.
• Fresh pineapple rings, ½-inch thick (4): Fresh pineapple caramelizes beautifully; canned won't give you that same textural contrast.
• Red onion, sliced into rings (1): The grill softens the sharpness while charring the edges just enough.
• Large tomato, sliced (1): Pick one that's actually ripe and fragrant—it's the fresh anchor for all the grilled richness.
• Avocado, sliced (1): Add this right before serving so it doesn't brown or get warm.
• Romaine or butter lettuce, large leaves (4): Sturdy enough to hold everything without wilting, but tender enough to eat raw.
• Cheddar or Swiss cheese slices (4, optional): Melts perfectly in the grill's heat, adding creaminess without overwhelming the other flavors.
• Mayonnaise or aioli (2 tablespoons): A thin drizzle brings richness and helps all the layers stick together.
• Fresh cilantro or parsley, chopped (1 tablespoon): Brightens everything with just a sprinkle.

Instructions

Make the Marinade and Coat the Chicken:

In a bowl, whisk together the olive oil, soy sauce, honey, smoked paprika, minced garlic, salt, and pepper until it's smooth and glossy. Place your chicken breasts in a dish and pour the marinade over them, making sure each piece gets coated. Let them sit for at least 15 minutes, though 2 hours will give you deeper, more complex flavor.

Get Your Grill Ready:

Preheat your grill or grill pan to medium-high heat and lightly oil the grates so nothing sticks. You'll know it's ready when you can hold your hand above it and feel the heat immediately.

Grill the Chicken Until Golden:

Place the chicken breasts on the hot grill and let them sit undisturbed for 5 to 6 minutes so they develop those beautiful caramelized marks. Flip them carefully and cook for another 5 to 6 minutes until the internal temperature reaches 165°F and the meat is no longer pink. If you're using cheese, lay the slices on top during the last 2 minutes so they melt gently.

Caramelize the Pineapple and Onions:

While the chicken cooks, place the pineapple rings on the grill for 2 to 3 minutes per side until they're deeply caramelized with charred edges. Do the same with the red onion rings, which should soften and develop a few black spots. The heat transforms their sharpness into something almost sweet.

Assemble Your Stacks:

On each plate, lay down a large lettuce leaf as your base—it's sturdy enough to hold everything. Top it with a grilled chicken breast, then a caramelized pineapple ring, followed by a grilled onion ring, fresh tomato slices, and avocado slices arranged however looks good to you.

Finish and Serve:

Drizzle a small amount of mayonnaise or aioli over the top and sprinkle with fresh cilantro or parsley. You can eat it as a open-faced stack as is, or place it on a toasted bun if you want something more traditional.

Save

The best moment with this dish came when my partner took a bite and closed his eyes for a second, then said something like, "This is what summer tastes like." That's exactly what I wanted—food that stops you, not because it's complicated, but because everything about it just works together.

The Magic of Grilled Fruit

Pineapple on a grill isn't a gimmick; it's a transformation. The sugars caramelize and concentrate, creating a sweet-savory contrast that plays perfectly against smoked chicken. The key is thickness—those ½-inch rings hold their shape and develop char on the outside while staying juicy inside. Once you discover this, you'll start grilling pineapple with everything.

Building Layers That Actually Work

These stacks are designed so every bite has something different happening. The warm grilled components sit on cool, crisp lettuce and fresh avocado, creating this rhythm between temperatures and textures. Start from the bottom with lettuce, then alternate warm and cool layers. This isn't overthinking it; it's the difference between a stack that holds together and one that falls apart after the first bite.

Customizing Without Losing the Thread

The beauty here is flexibility that still tastes intentional. Swap the chicken for grilled turkey or a quality plant-based patty and the whole dish still sings. You can skip cheese for dairy-free versions, or swap the mayo for a cilantro-lime aioli if you want something brighter. The structure stays the same, but you're cooking something that's actually yours.

• If you add chili flakes to the marinade, you'll get a subtle heat that complements the pineapple's sweetness.
• Serve these alongside sweet potato fries or a simple arugula salad tossed with lemon vinaigrette.
• A chilled Sauvignon Blanc pairs perfectly, as does a light, fruity Zinfandel if you prefer red.

Save

This is the kind of recipe that teaches you something without feeling like a lesson. Make it once, and you'll find yourself reaching for grilled pineapple long after summer ends.

Recipe FAQs

→ How do I prevent chicken from drying out on the grill?

Marinate the chicken before grilling to retain moisture and cook over medium-high heat, turning once to avoid overcooking.

→ What is the best way to caramelize pineapple on the grill?

Grill pineapple rings for 2–3 minutes per side until they develop golden grill marks and a sweet, caramelized surface.

→ Can I substitute the chicken with other proteins?

Yes, turkey or plant-based patties work well with the same marinade and grilling method for similar flavor profiles.

→ How can I make this dish dairy-free?

Omit the cheese slices and substitute mayonnaise or aioli with dairy-free alternatives to keep the flavors balanced.

→ What sides pair well with grilled chicken pineapple stacks?

Sweet potato fries, simple green salads, or grilled vegetables complement this dish nicely and enhance the meal’s freshness.