This grilled pineapple and chicken quesadilla recipe is one of those accidental weeknight wins that turned into a party favorite! Sweet, smoky, cheesy—all the good stuff wrapped in a golden, crispy tortilla. If you’re craving something tropical, comforting, and just a little fancy (without being fussy), grab your skillet and let’s bring a little sunshine to the table.
Why You’ll Love This Recipe
The first time I made these quesadillas, it was on a whim with some grilled pineapple from the night before—and my family hasn’t stopped requesting them since! They’re fresh, fast, and unexpectedly delicious.
- Sweet + Savory Combo: Grilled pineapple adds a caramelized sweetness that pairs beautifully with juicy chicken and melty cheese.
- Great for Leftovers: Use up leftover grilled chicken (or even a rotisserie bird!) and save yourself time.
- 30-Minute Meal: Weeknight dinner = handled.
- Kid-Friendly + Crowd-Pleasing: These quesadillas are basically guaranteed to vanish fast—so maybe make a second batch!
- Easy to Customize: Swap out proteins, cheeses, or even add a little heat depending on your vibe.
Ingredients Breakdown
Essentials
- 2 cups cooked chicken breast, shredded or sliced
- 1 cup fresh pineapple, grilled and chopped
- 2 cups shredded Monterey Jack cheese (or a blend)
- 1/2 red onion, thinly sliced
- 1/4 cup chopped fresh cilantro
- 1 tbsp olive oil or butter, for cooking
- 4 large flour tortillas
- Salt and pepper, to taste
Pro Tips
- Use rotisserie chicken to cut down on prep time.
- Grill the pineapple on a stovetop grill pan if you don’t have access to an outdoor grill—it still gives that smoky flavor.
- Add a handful of arugula for a peppery bite and a boost of green.
- Want some kick? Add sliced jalapeños or a drizzle of chipotle mayo inside.
Step-by-Step Instructions
- Heat a grill pan or outdoor grill to medium-high heat. Add pineapple slices and grill 2–3 minutes per side, until charred and caramelized. Let cool slightly, then chop.
- In a large skillet over medium heat, drizzle olive oil or melt butter. Place one tortilla in the pan.
- On half of the tortilla, layer 1/2 cup chicken, 1/4 cup grilled pineapple, a few red onion slices, a sprinkle of cilantro, and 1/2 cup cheese. Fold tortilla over to close.
- Cook 2–3 minutes per side, pressing gently with a spatula, until golden brown and cheese is melted.
- Transfer to a plate and repeat with remaining ingredients.
- Slice quesadillas into wedges and serve warm with salsa, sour cream, or guacamole.
Chef’s Tips and Tricks
- Don’t overfill the quesadillas—too much filling makes flipping tricky and messy.
- Let the quesadillas cool for a minute before slicing to keep the cheese from spilling out.
- Use a mix of cheeses for flavor and meltiness—cheddar, pepper jack, or even mozzarella.
- Press the quesadilla gently with a spatula as it cooks to help seal the layers.
Recipe Variations and Serving Suggestions
- Spicy Chicken Pineapple Quesadillas: Toss the chicken in buffalo or chipotle sauce before adding.
- Veggie Swap: Add grilled bell peppers or swap chicken for black beans and corn for a vegetarian version.
- Low-Carb Option: Make it with low-carb tortillas or turn the filling into a quesadilla bowl with rice or greens.
- Party Platter: Cut into smaller triangles and serve with a trio of dips—salsa, sour cream, and guac—for easy entertaining.
FAQs
Can I make these quesadillas ahead of time?
Yes! Assemble and store them in the fridge, then cook fresh before serving so they stay crispy.
What kind of cheese works best?
Monterey Jack is my go-to for meltiness and mild flavor, but a mix with cheddar or pepper jack adds great flavor, too.
Do I have to grill the pineapple?
You don’t have to—but grilling it adds that extra smoky depth without much effort. Totally worth the few added minutes!
Recipe Card
Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes
Ingredients:
- 2 cups cooked chicken breast, shredded
- 1 cup fresh pineapple, grilled and chopped
- 2 cups shredded Monterey Jack cheese
- 1/2 red onion, thinly sliced
- 1/4 cup chopped fresh cilantro
- 1 tbsp olive oil or butter
- 4 large flour tortillas
- Salt and pepper, to taste
Instructions:
- Grill pineapple slices 2–3 minutes per side. Chop and set aside.
- Heat oil or butter in a skillet. Add a tortilla and layer half with chicken, pineapple, onion, cilantro, and cheese. Fold in half.
- Cook 2–3 minutes per side until golden. Repeat with remaining ingredients.
- Slice and serve with favorite dips.
Nutrition: 425 calories per serving
If you loved these sweet-and-savory quesadillas, I’d love to hear how they turned out for you! Leave a comment, snap a photo, and tag @thekitchensaid on Instagram. Let’s see your kitchen magic!
