Grilled Hawaiian Chicken Sandwich

This classic Hawaiian-inspired chicken sandwich has become my go-to summer meal when I want to bring tropical vibes to our backyard cookouts. The combination of juicy marinated chicken, sweet grilled pineapple, and melty cheese creates an irresistible flavor explosion that transports you straight to paradise.

I first made these sandwiches for a beach-themed birthday party last summer, and they were such a hit that they've become a regular in our dinner rotation. My husband now requests them whenever we fire up the grill.

Ingredients

• Boneless skinless chicken breasts: Using thin slices ensures even cooking and the perfect meat-to-topping ratio.
• Pineapple rings: Fresh or canned both work beautifully. The natural sweetness caramelizes wonderfully on the grill.
• Soy sauce: Adds that savory umami depth to balance the sweetness. Low sodium prevents the marinade from becoming too salty.
• Brown sugar: Creates gorgeous caramelization and that signature Hawaiian sweetness.
• Dijon mustard: Provides tanginess and helps emulsify the marinade for better coating.
• Provolone cheese: Melts perfectly and its mild flavor complements without overwhelming the chicken and pineapple.
• Kaiser rolls or buns: Select ones sturdy enough to hold up to juicy fillings.
• Mayonnaise: Creates a protective barrier on the bun and adds creamy richness.
• Basic seasonings: Salt, pepper, and garlic powder create the perfect flavor foundation.

Step-by-Step Instructions

Prepare the chicken:

Start with even thickness chicken by pounding breasts to about 1-inch thickness then slicing each in half to create four equal portions. Season both sides generously with salt, pepper, and garlic powder. This simple seasoning base allows the marinade flavors to shine while ensuring the chicken itself is well seasoned.

Create the marinade:

Combine pineapple juice from the can with soy sauce, brown sugar, and Dijon mustard, whisking until the sugar dissolves completely. This sweet tangy umami-rich mixture will transform ordinary chicken into something extraordinary. Place the chicken in the marinade making sure each piece is fully submerged, and refrigerate overnight for maximum flavor penetration.

Grill the chicken:

Preheat your grill to medium-high heat approximately 375-400°F ensuring the grates are well oiled to prevent sticking. Place marinated chicken pieces directly over the heat source cooking for approximately 6-7 minutes per side or until the internal temperature reaches 165°F. During the final 3 minutes of cooking top each chicken piece with a slice of provolone allowing it to melt perfectly over the hot chicken.

Grill the pineapple:

Add pineapple rings to the grill when the chicken is halfway done approximately 6 minutes before completion. Grill each side for about 3 minutes until you see those beautiful caramelized grill marks develop. The heat transforms the pineapple concentrating its sweetness and adding a subtle smokiness.

Assemble the sandwiches:

Spread a thin layer of mayonnaise on both halves of your toasted buns. This creates a moisture barrier that prevents the buns from becoming soggy. Place a piece of cheese-topped chicken on the bottom half, followed by a grilled pineapple ring. Add the top bun and serve immediately while everything is still warm and the cheese is gloriously melty.

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The first time I served these sandwiches my daughter who normally picks pineapple off pizza devoured her entire sandwich and asked for seconds. Something about the grilling process transforms the pineapple making it caramelized and less acidic which converted her instantly. Now this recipe has become our special father-daughter cooking project when we want to surprise mom with dinner.

Marinating Magic

The overnight marinade is truly what makes these sandwiches special. The pineapple juice contains enzymes that naturally tenderize the chicken while infusing tropical flavor into every bite. The brown sugar helps create gorgeous caramelization when grilled while the soy sauce adds depth and umami notes. If you're in a hurry you can reduce marinating time to 4 hours but the flavor won't penetrate quite as deeply. For meal prep you can freeze the chicken in the marinade for up to 3 months then thaw overnight in the refrigerator when ready to use.

Smart Substitutions

These sandwiches are incredibly versatile and can be adapted to suit various dietary needs or what you have on hand. For a lighter version use Greek yogurt instead of mayonnaise or skip the cheese altogether. Chicken thighs work beautifully as a substitute for breasts offering even more juiciness and flavor though they may need slightly longer cooking time. Not a fan of provolone? Swiss cheese or pepper jack work wonderfully too. For a gluten-free option serve the chicken and pineapple over a bed of coconut rice instead of on a bun or use your favorite gluten-free rolls.

Serving Suggestions

Turn this into a complete tropical feast by serving with coconut rice, cilantro lime slaw, or a simple green salad with mango. For drinks consider fresh pineapple juice blended with coconut cream or a light lager beer. These sandwiches also pair beautifully with sweet potato fries or grilled corn on the cob for a complete summer meal. For an extra special touch, offer additional toppings like sliced avocado, red onion rings, bacon, or a pineapple jalapeño salsa for guests to customize their sandwiches.

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Common Queries

→ Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works perfectly and provides a vibrant flavor. Slice it into rings and pat dry before grilling.

→ How do I make sure the chicken stays tender?

Marinating the chicken overnight in the pineapple-soy mixture helps lock in moisture and adds incredible flavor.

→ Can I cook these without a grill?

Yes, you can use a stovetop grill pan or bake the chicken in the oven at 375°F until it reaches 165°F internally.

→ What other cheese options work well?

Swiss cheese or mozzarella are great alternatives if you don’t have provolone. They melt nicely and complement the flavors.

→ Can I make this meal ahead of time?

You can marinate the chicken the day before and grill it just before serving. Reheat gently to avoid drying out.