Grilled Chicken and Pineapple Quesadillas: The Ultimate Sweet & Savory Fiesta

Tropical sweetness and protein unite for a fuss free meal that pleases every crowd.

By Sneha Tete, Integrated MA, Certified Relationship Coach
Created on

Grilled Chicken and Pineapple Quesadillas

Bring vibrant flavor, quick satisfaction, and a hint of tropical sweetness to your table with grilled chicken and pineapple quesadillas. This recipe unites tender grilled chicken, juicy fresh pineapple, and plenty of melted cheese in an easy, weeknight-friendly format—ready for a fiesta or a family meal.

Why You’ll Love This Recipe

  • Quick & simple: Ready in under 45 minutes with minimal prep.
  • Crowd-pleasing: Kid-friendly and sure to impress adults.
  • Perfect balance: Sweet pineapple complements smoky chicken and gooey cheese.
  • Versatile: Ideal for lunch, dinner, or party appetizers.
  • Customizable: Swap proteins, cheeses, or add your favorite veggies!

Ingredient Breakdown

This recipe keeps things simple and accessible, using everyday ingredients with an emphasis on flavor. Here’s a closer look at what you’ll need:

  • Chicken breasts: Boneless, skinless for easy grilling and slicing.
  • Pineapple: Fresh rings or spears provide caramelized sweetness; canned will work in a pinch.
  • Monterey Jack cheese: Melts beautifully and blends easily with other ingredients.
  • Cheddar cheese (optional): Adds tangy, sharp richness to each bite.
  • Tortillas: Large, flour tortillas offer the classic quesadilla texture.
  • Olive oil: For brushing chicken, pineapple, and the tortillas before grilling.
  • Salt and pepper: For seasoning.
  • Optional extras: Jalapeños, cilantro, red onion, or other fresh veggies for kick and crunch.

For a full ingredients list and quantities, see the detailed recipe card below.

Step-by-Step Instructions

Follow these steps for perfect grilled chicken and pineapple quesadillas every time:

  1. Prep the grill:

    Heat your grill or grill pan to medium-high. Brush grates with oil or spray to prevent sticking.

  2. Season the chicken:

    Pat chicken breasts dry, then brush with olive oil and sprinkle liberally with salt and pepper on both sides.

  3. Grill the chicken:

    Place on hot grill and cook for 5-7 minutes per side, until internal temperature reaches 165°F (74°C). Remove and allow to rest for a few minutes.

  4. Grill the pineapple:

    Brush pineapple slices or spears with olive oil. Grill 2-3 minutes per side until browned and caramelized.

  5. Slice ingredients:

    Thinly slice grilled chicken and chop pineapple into bite-sized chunks for even distribution in each quesadilla.

  6. Assemble quesadillas:

    Lay out tortillas and fill half of each with sliced chicken, pineapple, and plenty of cheese. Fold tortillas over to create half-moon shapes.

  7. Grill quesadillas:

    Brush outside of quesadillas lightly with olive oil. Grill 1-2 minutes per side until golden brown and cheese is melted. Alternatively, use a skillet on the stovetop for small batches.

  8. Slice and serve:

    Let quesadillas cool briefly, then slice into wedges. Serve immediately with your favorite sides or dips.

Detailed Recipe Card

IngredientAmountNotes
Chicken breasts2 largeBoneless & skinless
Pineapple4-6 slicesFresh preferred (canned okay)
Monterey Jack cheese1 ½ cups shreddedCan substitute with a blend
Cheddar cheese½ cup shreddedOptional for more flavor
Flour tortillas4 extra-largeBurrito size works best
Olive oil2 tbspFor brushing/grilling
Salt & pepperTo taste
Optional: jalapeño, cilantro, red onionAs desiredAdd-ins for flavor

Topping & Serving Suggestions

  • Classic salsa: Tomato salsa or pico de gallo adds fresh, bright flavor.
  • Guacamole: Creamy avocado dip balances the tartness of pineapple.
  • Sour cream: A dollop cools the palate and pairs well with the grilled notes.
  • Sriracha mayo: For those who love a spicy kick.
  • Cilantro and fresh lime: Sprinkle over wedges for zest and pop.

Recipe Tips & Variations

  • Marinate for flavor: Add a citrusy or spicy marinade to the chicken before grilling for extra depth.
  • Use leftover chicken: Rotisserie chicken or leftovers work well—just warm before assembling.
  • Vegetarian option: Substitute grilled portobello mushrooms or sweet potato for chicken.
  • Cheese options: Try pepper jack, mozzarella, or queso fresco for different flavor profiles.
  • Tortilla swaps: Use whole wheat or gluten-free tortillas to suit dietary needs.
  • Pineapple alternatives: Mango or peaches work for a fresh twist if pineapple isn’t on hand.
  • Make it a meal: Serve with Mexican rice, beans, or a crunchy slaw.

Make-Ahead & Storage Guide

  • Prep ahead: Grill chicken and pineapple up to 2 days ahead and refrigerate in airtight containers.
  • Reheating: Quesadillas reheat best in a skillet over low heat. Avoid the microwave for crispness.
  • Freezing: Assemble quesadillas, wrap tightly in foil, and freeze up to 2 months. Thaw and grill as usual.
  • Leftovers: Store in fridge up to 3 days. Reheat before serving.

Nutrition & Dietary Info

Serving SizeCaloriesProteinFatCarbs
1 quesadilla wedge (1/4th of recipe)~35023g14g35g

Nutrition values are estimates and will vary based on add-ins and type/quantity of cheese and tortillas.

Frequently Asked Questions (FAQs)

Can I make these quesadillas without a grill?

Yes. Use a grill pan or a stovetop skillet. Sear chicken and pineapple for similar caramelization, then cook assembled quesadillas in the same pan.

What kind of cheese works best?

Monterey Jack is recommended for its melt and mild flavor. Mixing in cheddar or pepper jack adds extra tang or spice.

How can I keep quesadillas crispy?

Brush tortillas lightly with oil and cook on medium-high heat. Do not overcrowd the pan. Serve immediately after slicing.

What dips go well with these quesadillas?

Salsa, guacamole, sour cream, chipotle mayo, or fruity salsas are all excellent partners.

Can I use canned pineapple?

Fresh pineapple yields more flavorful caramelization, but canned can be used in a pinch. Drain and pat dry before grilling.

Are these quesadillas gluten-free?

Use gluten-free tortillas and check each ingredient. Chicken and pineapple are naturally gluten-free.

How many does this recipe serve?

The recipe makes four large quesadillas; each serves 1-2 people depending on sides.

Pro Tips for Perfect Quesadillas

  • Shred cheese freshly: Pre-shredded cheese contains anti-caking agents and doesn’t melt as smoothly.
  • Rest grilled chicken: Allows juices to redistribute for tender slices.
  • Don’t overfill: Too much filling makes quesadillas messy and harder to handle.
  • Cut with pizza wheel: For clean, neat wedges.
  • Serve hot: They are best enjoyed warm and fresh off the grill.

Creative Variations & Pairings

  • Barbecue twist: Toss chicken in barbecue sauce before assembling for smoky-sweet fusion.
  • Spicy Hawaiian: Add jalapeños to the filling or serve with pineapple salsa spiked with hot sauce.
  • Breakfast quesadillas: Add scrambled eggs to the filling for a hearty morning meal.
  • Tropical slaw: Serve with a crunchy pineapple-cabbage slaw.
  • Margarita pairing: Enjoy with a classic margarita or a pineapple mojito to complement flavors.

Related Recipes

  • Classic Chicken Quesadillas
  • Pineapple Salsa
  • Grilled Veggie Quesadillas
  • Guacamole

Recipe Summary

Prep Time15 minutes
Cook Time25 minutes
Total Time40 minutes
Servings4 large quesadillas

Author Notes

Grilled chicken and pineapple quesadillas strike the perfect flavor balance between smoky, sweet, and savory. This recipe is easy to adapt for all tastes and occasions—expand, swap, or elevate ingredients as you wish. The method suits busy families, casual parties, and picky eaters alike. Enjoy your fiesta!

Sneha Tete
Sneha TeteBeauty & Lifestyle Writer
Sneha is a relationships and lifestyle writer with a strong foundation in applied linguistics and certified training in relationship coaching. She brings over five years of writing experience to thebridalbox, crafting thoughtful, research-driven content that empowers readers to build healthier relationships, boost emotional well-being, and embrace holistic living.

Read full bio of Sneha Tete