Grilled Pineapple and Chicken Quesadillas are easy and delicious dinner! Chicken, cheese, and little barbecue sauce.

Grilled Chicken and Pineapple Quesadillas


In the past three weeks we’ve scared away three babysitters. I’m starting to question if my parenting skills are really that bad or if my two-year-old Wes is just the sweetest devil you’ll ever know.

Babysitter #1: I texted her and told her we were on her way home from our date and asked if the boys were asleep (we took baby Gracie with us). She said she “Um…no. I actually had to call my mom because it got that bad.” Great. She said in her Southern drawl that Wes had ripped off all of his clothes and was “nek-ked” yelling at her and running around the house refusing to do anything she said.

Although embarrassing, it wasn’t all that surprising to me. Wes often finds his clothes restricting and tries to get naked whenever we aren’t looking. And I can’t say it would be the first naked defiant tantrum that he’s thrown. He’s two and good at it. I chalked up the situation to the inexperience of a 16-year-old to handle a grouchy two-year-old and moved on.

Babysitter #2: I was really nervous about leaving my baby for the first time but we were headed to a work event for my husband and bringing a baby just wasn’t appropriate.

The babysitter was a 25-year-old who is a full-time nanny for a family with 3 children so I figured she could handle it. After many discussions about whether she was comfortable watching my three boys and a 5-month old she said “Oh yeah, I can handle it.”

After being gone for one hour I got a text from her saying, “I can’t handle this. I called my mom to come hold the baby.” I guess baby Gracie wouldn’t stop crying and missed her mama. So I headed home thinking, “Am I supposed to pay her and her mom?”

Babysitter #3: Itstarted off well. I didn’t dare leave Gracie after the last fiasco so we took her with us with some friends to the movies. She’s really good and never makes a peep as long I’m holding her.

Halfway through the movie the babysitter calls. “Um…Wes locked me in his bedroom and I can’t get out.”

We switched the door handle on his bedroom so that the lock is on the outside and she had tried to get him in his room to read a book and he locked her and the other boys in there. Smart and mischievous are a bad combination.

So that’s it. I’ve decided to never leave the house again. Ever.

These Grilled Pineapple and Chicken Quesadillas are easy and delicious!
 These Grilled Pineapple and Chicken Quesadillas were definitely my kid’s favorite dish from “Get Your Grill On” week. Sweet pineapple with cheese and chicken in a buttery tortilla really is a great combination.
Grilled pineapple is one of our favorite healthy desserts. The natural sugars start to caramelize and it turns into a delicious treat.
Grilled Chicken and Pineapple Quesadillas

Layer your tortilla with chicken and slices of pineapple. Top it with additional BBQ sauce. You could add jalapenos here for some added kick but our BBQ sauce was pretty spicy so it didn’t need anything.


Grilled Pineapple and Chicken Quesadillas

4.50 from 4 votes
These Grilled Pineapple and Chicken Quesadillas are easy and delicious!
Prep Time: 10 minutes
Cook Time: 10 minutes
Total Time: 20 minutes
Servings: 8 servings


  • 8 whole flour tortillas
  • butter
  • 2 cups grilled pineapple, sliced
  • 3 skinless, boneless chicken breasts pounded thin or butterflied
  • salt and pepper, to taste
  • 3 cups shredded Monterey Jack cheese
  • 3 tablespoons spicy barbecue sauce
  • optional cilantro and jalapenos


  • To grill pineapple: Cut wedges, stick on skewers, and grill over low heat either on a grill, grill pan, or even a skillet. Cut into slices.
  • Sprinkle chicken with salt and pepper and Cajun spice if you want some heat. Spray grill with cooking spray and grill on both sides until done, brushing with barbecue sauce after it's finished. Set aside and slice into very thin slices.
  • Warm pan over medium heat and put butter in the pan enough to coat. Slightly warm and toast tortillas on both sides, then remove from griddle and set aside.
  • To assemble, sprinkle four browned tortillas with grated Monterey Jack and arrange chicken slices and pineapple slices evenly over the surface. If desired, add sliced jalapenos and cilantro here. Drizzle extra barbecue sauce over the top. Add second browned tortilla on top of each one. (You'll have four complete quesadillas at this point.)
  • Add quesadillas back to skillet to warm, until cheese is melted. Cut each quesadilla into six wedges. Serve with sour cream, pico de gallo, and lime wedges.


Cuisine: American
Course: Main Course
Grilled Chicken and Pineapple Quesadillas