This Grilled Hawaiian Chicken Sandwich quickly became my go-to for warm-weather dinners. I first made it on a bright July afternoon when I had leftover pineapple from a barbecue and two boneless chicken breasts in the fridge; the combination of sweet pineapple juice, brown sugar, and soy sauce turned the simple chicken into something that tasted like a beachside cookout. The sandwich balances sweet, salty, and tangy elements: the marinated chicken caramelizes on the grill, the pineapple rings get a bit of char and extra sweetness, and the provolone melts into a silky blanket over the meat. Every bite is a little tropical vacation.

I usually marinate the chicken overnight — the extra time makes a huge difference in flavor and tenderness — but if you're pressed for time, even two hours will improve the taste. My kids love that the pineapple adds a juicy burst, and guests are always surprised at how easy it is to produce such a crowd-pleasing sandwich. It’s become the highlight of summer lunches and casual dinners: fresh buns, a smear of mayo, and the smells of caramelization make the whole family gather around the table.

Ingredients

• Chicken: Use two 6-ounce boneless, skinless breasts — they’re easy to portion and grill evenly after pounding to 1-inch thickness. If shopping, pick fresh breasts with a pale pink color and firm texture.
• Seasonings: 1/2 teaspoon coarse salt, 1/4 teaspoon black pepper, 1/4 teaspoon garlic powder — simple dry seasoning underlines the marinade without competing with pineapple sweetness.
• Pineapple: An 8-ounce can of pineapple rings (juice reserved) or fresh rings — canned is convenient and the juice makes an excellent marinade base; fresh provides brighter acidity and firmer rings.
• Marinade: 2 tablespoons low-sodium soy sauce, 2 tablespoons packed brown sugar, 2 teaspoons Dijon mustard mixed with the pineapple juice — this trio builds umami, sweetness, and a touch of zing.
• Cheese: Four slices of provolone melt nicely without overpowering the sweetness; substitute Monterey Jack or cheddar for a different finish.
• Buns: Four burger buns or kaiser rolls, toasted lightly so they stand up to the juicy chicken and pineapple.
• Finish: 1/4 cup mayonnaise — a thin smear adds silkiness and balances acidity without masking the flavors.

Instructions

Prepare and portion the chicken: Pound each breast with a meat mallet between plastic wrap until an even 1-inch thickness; if breasts are larger, slice each in half horizontally so you end up with four even pieces. Even thickness ensures uniform cooking and prevents dry edges. Pat dry with paper towels, then season both sides with the coarse salt, black pepper, and garlic powder. Make the marinade and marinate: Combine the juice from the pineapple can (about 1/3 cup), 2 tablespoons low-sodium soy sauce, 2 tablespoons packed brown sugar, and 2 teaspoons Dijon mustard in a shallow dish. Whisk until sugar dissolves. Add the chicken pieces, turning to coat. Cover and refrigerate at least 2 hours, preferably 12 hours or overnight, for maximum flavor penetration — the acid in the pineapple gently tenderizes while the soy and sugar caramelize on the grill. Preheat and oil the grill: Preheat a gas or charcoal grill to medium-high (about 400–450°F). Clean the grates thoroughly and oil them using a paper towel dipped in vegetable oil and tongs to prevent sticking. A hot, well-oiled grate promotes good sear marks and prevents tearing the meat when flipping. Grill the chicken: Place chicken on the hot grill and cook 12–15 minutes total, flipping once halfway through. The goal is an internal temperature of 165°F measured at the thickest part with an instant-read thermometer. Look for deep grill marks and golden caramelization from the brown sugar in the marinade. Add cheese and pineapple: About 3 minutes before the chicken is done, top each piece with a slice of provolone and close the lid to melt. Add the pineapple rings to the grill halfway through the chicken cook time and turn once; pineapple should develop grill marks and slightly caramelize (about 2–3 minutes per side). Assemble the sandwiches: Lightly toast buns on the grill for 30–60 seconds. Smear 1 tablespoon mayonnaise on each bun, top with a piece of chicken, then a grilled pineapple ring, and close. Serve immediately while hot and juicy.

Storage Tips

Store leftover grilled chicken and pineapple in separate airtight containers in the refrigerator for up to 4 days. If you want to freeze, cool completely then wrap chicken pieces tightly in plastic wrap and place in a freezer bag; freeze up to 3 months. Thaw overnight in the refrigerator and reheat gently on low heat or in a 325°F oven until warmed through. Toast buns right before serving to avoid sogginess, and keep mayonnaise separate until assembly if preparing meals ahead.

Ingredient Substitutions

If you don’t have provolone, Monterey Jack or a mild cheddar work well; for a smoky note try smoked gouda. Replace low-sodium soy sauce with tamari for a gluten-free option and use gluten-free buns to make the sandwich suitable for celiac diets. For a dairy-free version, omit cheese and swap mayonnaise for a dairy-free aioli. If you prefer less sweetness, reduce brown sugar to 1 tablespoon or add 1 teaspoon rice vinegar to the marinade for extra tang.

Serving Suggestions

Serve with a crisp green salad or a crunchy cabbage slaw to cut through the sweetness; cole slaw with a touch of rice vinegar complements the flavors perfectly. For sides, grilled corn on the cob or sweet potato fries are great matches. Garnish sandwiches with thinly sliced red onion or fresh cilantro for a bright contrast, and offer pickled jalapeños on the side for guests who want heat.

Cultural Background

This sandwich takes inspiration from Hawaiian-style grilling where fruit and meat are often paired — pineapple was popularized in Hawaiian cuisine through both indigenous usage and later agricultural development. Combining sweet grilled fruit with savory protein shows up across Pacific and American coastal cuisines; this handheld version is an Americanized adaptation ideal for backyard barbecues and family gatherings.

Seasonal Adaptations

In summer use fresh pineapple rings for brighter flavor and firmer texture; during cooler months canned rings are a convenient alternative. For a winter twist, substitute grilled pears or apple slices brushed with a little brown sugar and butter. Add a smear of cranberry chutney at holiday meals to bring festive acidity alongside the savory chicken.

Meal Prep Tips

Marinate chicken the night before and grill all pieces on the same day for quick assembly. Keep buns and condiments separate and pack sandwiches just before serving to avoid sogginess. For packed lunches, include a small container of mayonnaise or aioli and reheat chicken in a microwave-safe container for 45–60 seconds, then assemble with room-temperature pineapple.

Make these sandwiches your own: experiment with sriracha mayo, grilled peppers, or adding a handful of baby arugula for peppery brightness. The combination of sweet grilled pineapple, savory marinated chicken, and melted provolone makes for an unforgettable, easy-to-execute meal that will become a summer staple in your rotation.