If you ask me, grilled chicken sandwiches are always a good idea.

This sweet and savory sandwich brings together juicy grilled chicken and caramelized pineapple for a taste that feels like summer. The chicken soaks up a simple soy and pineapple juice marinade that gives it tons of flavor.

It’s topped with melted provolone, grilled pineapple rings, and crisp red onion on a soft bun. A quick swipe of mayo keeps everything moist and helps the flavors come together.

It’s a satisfying meal that works great for a weeknight dinner or weekend cookout.

Why You’ll Love This Grilled Pineapple Chicken Sandwich

Quick weeknight dinner – Ready in just 20-30 minutes, this sandwich is perfect for busy evenings when you want something delicious without spending hours in the kitchen.
Sweet and savory flavor combo – The grilled pineapple paired with tender chicken creates that perfect balance of flavors that makes every bite interesting.
Simple ingredients – You probably have most of these items in your pantry already, and the ingredient list is short and straightforward.
Family-friendly meal – Kids and adults alike love this sandwich, making it an easy win for dinner that everyone will actually eat.
Works for any occasion – Whether you’re firing up the grill for a casual weeknight or hosting a summer cookout, these sandwiches fit right in.

What Kind of Chicken Should I Use?

For this recipe, boneless, skinless chicken breasts are your best bet since they cook evenly on the grill and are easy to slice for sandwiches. If your chicken breasts are on the thicker side (more than about an inch thick), you’ll want to pound them to an even thickness so they cook through at the same rate as the pineapple. You can also use chicken cutlets if you find them at the store, which are already thin and will save you some prep time. Fresh chicken is always great, but if you’re working with frozen breasts, just make sure they’re completely thawed and patted dry before seasoning and grilling.

Options for Substitutions

This sandwich is pretty forgiving when it comes to swaps, so here are some options:

Chicken breasts: Boneless, skinless chicken thighs work great here and stay juicier on the grill. You can also use turkey cutlets if you prefer, just watch the cooking time since they cook faster.
Pineapple rings: Fresh pineapple is always best if you can get it – just slice it into 1/2-inch thick rounds. Canned works perfectly fine too, just make sure to pat them really dry so they’ll caramelize on the grill.
Provolone cheese: Swiss, mozzarella, or pepper jack all melt nicely on this sandwich. Go with pepper jack if you want a little kick.
Soy sauce: Coconut aminos or tamari work as substitutes. If using regular soy sauce instead of low sodium, cut the amount to 1 tablespoon to avoid making it too salty.
Buns: Brioche buns, ciabatta rolls, or even regular hamburger buns all work. Just toast them lightly on the grill for extra flavor.
Mayonnaise: Greek yogurt mixed with a squeeze of lemon makes a lighter spread, or you can use your favorite aioli for more flavor.

Watch Out for These Mistakes While Grilling

The biggest mistake when grilling chicken breasts is not flattening them to an even thickness, which leads to dry edges while the center is still cooking – aim for a consistent 1-inch thickness by pounding with a meat mallet or the bottom of a heavy pan.

Another common error is flipping the chicken too many times or pressing down on it with your spatula, which squeezes out all those flavorful juices and leaves you with dry meat – flip just once and let it cook undisturbed.

Don’t forget to pat those pineapple rings completely dry before they hit the grill, otherwise they’ll steam instead of getting those nice caramelized grill marks, and make sure your grill grates are clean and well-oiled to prevent sticking.

Finally, resist the urge to cut into the chicken right away – let it rest for 5 minutes after grilling so the juices redistribute throughout the meat instead of running all over your cutting board.

What to Serve With Grilled Pineapple Chicken Sandwich?

These sandwiches are pretty filling on their own, so I like to keep the sides simple and let the sweet and savory flavors shine. A batch of crispy sweet potato fries or regular fries is always a winner, and they’re perfect for dipping into extra mayo or even some sriracha mayo if you want a little kick. For something lighter, try a crunchy coleslaw or a simple cucumber salad to balance out the richness of the sandwich. If you’re firing up the grill anyway, throw on some corn on the cob or zucchini spears for an easy veggie side that fits right in with the tropical vibe.

Storage Instructions

Store: If you have leftover grilled chicken and pineapple, keep them separate from the buns in an airtight container in the fridge for up to 3 days. The buns will get soggy if you assemble the sandwiches ahead, so it’s best to store everything separately and put it together when you’re ready to eat.

Make Ahead: You can marinate the chicken in the soy sauce mixture up to 24 hours before grilling, which actually makes it even more flavorful. Just keep it covered in the fridge until you’re ready to cook. The pineapple can also be prepped and patted dry a day ahead.

Serve: To enjoy your leftovers, warm the chicken and pineapple in a skillet over medium heat for a few minutes until heated through. You can also microwave them for about 30-45 seconds, then add fresh cheese and assemble on a toasted bun for the best texture.

Preparation Time	10-15 minutes
Cooking Time	10-15 minutes
Total Time	20-30 minutes
Level of Difficulty	Medium
Servings	4 sandwiches

Estimated Nutrition

Estimated nutrition for the whole recipe (without optional ingredients):

Calories: 1300-1500
Protein: 90-105 g
Fat: 45-55 g
Carbohydrates: 140-160 g

Ingredients

For the chicken:

12 oz chicken breasts (cut into 1/2-inch thick cutlets for even grilling)
1/2 tsp salt
1/4 tsp pepper
1/2 tsp garlic powder
1/4 tsp smoked paprika
4 slices provolone (I prefer Boar’s Head for a better melt)

For the marinade:

8 oz pineapple juice (I use Dole for the most consistent sweetness)
3 tbsp soy sauce
2 tbsp brown sugar
1 tbsp mustard

For assembly:

4 pineapple rings (patted dry to ensure better caramelization)
4 buns
1/4 cup mayonnaise (I always use Hellmann’s for the creamiest texture)
4 thin slices red onion

Step 1: Prepare the Chicken and Create the Marinade

12 oz chicken breasts
1/2 tsp salt
1/4 tsp pepper
1/2 tsp garlic powder
1/4 tsp smoked paprika
8 oz pineapple juice
3 tbsp soy sauce
2 tbsp brown sugar
1 tbsp mustard

Start by cutting the chicken breasts into 4 even pieces, then pound each to a uniform 1/2-inch thickness—this ensures they’ll cook evenly on the grill.

While the chicken is still on your work surface, season both sides generously with salt, pepper, garlic powder, and smoked paprika, pressing the spices in gently so they adhere well.

In a separate bowl, whisk together the pineapple juice, soy sauce, brown sugar, and mustard until the sugar dissolves completely.

Place the seasoned chicken in a zip-top bag or shallow dish, pour the marinade over it, and refrigerate for at least 2 hours (or overnight for deeper flavor).

I find that even a 2-hour marinade develops plenty of flavor if you’re short on time, though overnight is ideal.

Step 2: Prepare the Ingredients for Assembly

4 pineapple rings
4 thin slices red onion
1/4 cup mayonnaise
4 buns
4 slices provolone

While the chicken marinates, pat the pineapple rings completely dry with paper towels—this is crucial for achieving a nice caramelized crust rather than steaming them on the grill.

Slice the red onions into thin slices and set aside.

Spread the mayonnaise evenly on the inside of all 4 buns and set them on a clean surface, ready for assembly.

Have the provolone slices ready as well.

This prep work takes just a few minutes but makes the final assembly seamless once everything is hot off the grill.

Step 3: Grill the Chicken and Pineapple

marinated chicken from Step 1
pineapple rings from Step 2

Preheat your grill to medium-high heat (around 400°F if using a gas grill).

Remove the chicken from the marinade and let any excess drip off, then place the pieces directly on the grill grates.

Cook for about 6-7 minutes without moving them, which allows the spices to caramelize and creates beautiful grill marks.

After about 6 minutes, add the pineapple rings to a cooler part of the grill or on the outer edge—they’ll need about 6-8 minutes total, getting flipped once halfway through.

When the chicken has cooked for about 12 minutes total (6 minutes per side), it should register 165°F on a meat thermometer.

I like to flip the chicken only once to keep those grill marks intact and let the pineapple caramelize undisturbed.

Step 4: Add Cheese and Finish Grilling

4 slices provolone

During the final 2-3 minutes of grilling the chicken, place one slice of provolone on top of each chicken cutlet.

If your grill has a lid, close it to help the cheese melt faster—it should become soft and slightly bubbly.

If you don’t have a lid, you can tent the chicken loosely with foil.

The cheese will continue to melt off the grill if needed, but getting it warm and pliable while still grilling is ideal.

Step 5: Assemble and Serve

grilled chicken from Step 3
grilled pineapple from Step 3
red onion from Step 2
buns with mayo from Step 2

Remove the chicken and pineapple from the grill and let the chicken rest for just 1-2 minutes—this keeps the juices from running out when you bite into it.

Place one piece of grilled chicken with melted cheese on each mayo-spread bun, then top with a grilled pineapple ring.

Add a few slices of fresh red onion on top of the pineapple for a pop of color and a sharp, fresh contrast to the sweet and savory flavors.

Serve immediately while everything is still warm.