Grilled Chicken & Pineapple Quesadillas

Last Saturday’s dinner was an easy, one (just the way I like it)! I always feel like I have all this time on my hands on Saturdays, then some how, it turns into 5 o’clock at night and I’m just starting my cooking and baking. I just don’t know where my time goes!

I’ve mentioned previously that I wanted to cook and bake at least once every weekend. The night for that is usually Saturdays because I [usually] have an entire day for whatever it is I want to do.

I found a recipe for grilled chicken and pineapple quesadillas on The Pioneer Woman’s blog and I knew right away that was what I wanted to make. It’s a very hands-on recipe, not like a chicken parm that you leave in the oven for an hour and it’s done. This takes grilling the chicken and pineapple, toasting the quesadilla shells one by one, assembling, and then again, putting them back on the skillet. Somehow, I consider this an easy recipe.

The Pioneer Woman cuts up an entire pineapple. I figured I’d save myself some time and a finger or two and buy the pre-cut pieces. I highly recommend this. Grilling them is super easy, and even easier if you have a skewer. The pineapple makes this recipe in my opinion, so don’t leave it out. I mixed the chicken around in a Frank’s Red Hot Sweet Heat BBQ sauce to give it some kick and the pineapple added a really nice sweet taste to it.

The official recipe is linked at the bottom of this post, but I took a few pictures to show you the assembly process =)

First, toast up your quesadilla wraps by adding some olive oil to a hot skillet, larger than the wrap itself. Flip it over after a minute or two just so each side is nice and toasty.

Then, add your chicken…
I cut mine into strips because The Pioneer Woman did and I’m pretty sure she knows what she’s doing in life.

Then, add your pineapple, cheese, and jalapeño pieces (not show in picture, but I did add them, and they are awesome! If you like hot, put these bad boys on).

Then, top this beauty off with another toasted quesadilla wrap and return it to the hot skillet with some olive oil. It gets this awesome crispy, golden-brown outside.

There you have it! Grilled chicken and pineapple quesadillas. I paired it with a corn chowder, a mix my sister got me from the deep south. It was yummy.

You know what else would be great with this? A tequila mockingbird. That’s a whole other post for a whole other time. But I’ll give you a little hint: tequila, pineapple juice, chambord. There’s more to it, but that’s all you get for now. If you really want the recipe, I’ll find it in my heart to give it to you. Heck, of course I’ll give it to you! I need to share this fabulous drink with the world. I, however, cannot take credit for it. Big shout out to Mel here: Mel created this drink and named it, and it’s fabulous!

Enjoy this tasty meal, and don’t forget some avocado and sour cream!

Grilled Chicken & Pineapple Quesadillas from The Pioneer Woman

  • 8 whole Flour Tortillas
  • Butter Or Margarine
  • 2 cups Grilled Pineapple, Sliced
  • 3 whole Boneless, Skinless Chicken Breasts
  • Salt And Pepper, to taste
  • 3 cups Monterey Jack Cheese, Grated
  • 1 whole Jalapeno, Sliced
  • Cilantro
  • 3 Tablespoons Barbecue Sauce


(To grill pineapple: stick wedges on skewers, and grill over low heat. Cut into slices.)
(To pound chicken, place inside a Ziploc bag and pound with a mallet or large can to flatten to uniform thickness.)

Sprinkle with salt and pepper and Cajun spice (or cumin/cayenne, etc.) Drizzle olive oil on a grill pan and grill on both sides until done, brushing with barbecue sauce. Set aside and slice into very thin slices.
Warm griddle over medium heat and put sizzling butter or margarine [I used olive oil] in the pan. 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. Arrange chicken slices evenly over the surface. Add pineapple slices and jalapeno slices. Sprinkle on cilantro [I didn’t use any cilantro]. If desired, 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 to oven to warm, or back to skillet to warm, until cheese is melted. Cut each quesadilla into six wedges. Serve with sour cream, avocado, pico de gallo, and lime wedges. Yum!