Crock-Pot Crazy Pineapple Chili

by Shelley · May contain affiliate links

Published Updated April 5, 2023

~ Contest-winning chili with an amazing flavor twist that people go crazy over! Quick and easy in the slow cooker – and healthy, too! A guaranteed win! ~

This Recipe Is:     Freezable    Make Ahead    Gluten Free  

Crock-Pot Crazy Pineapple Chili Recipe {}

It may be a little crazy, but this chili doesn’t mess around!

It’s a mega-award winner, one chili cook-off after another.

Not those national kind of cook-offs where professional contest-entering-folks compete to see who can concoct the most bizarre kluge of unrelated ingredients.

Nope! This one wins all those neighborhood and workplace contests. You know – the cook-offs where real people enter the really-truly-best chili they’ve ever tasted, the recipe they always, always make. And you just know that to win those contests, it’s gotta be really, truly good.

Crazy? Yep!

Really and truly good? You betcha!

Crock-Pot Crazy Pineapple Chili Recipe {}

Oh, sure – I know the pineapple has you kinda scratching your head. Huh? Pineapple? In chili???

You’re intrigued but a little wary, right? I understand! I’ve been there!

I first heard the legend of Crazy Pineapple Chili from my dear, dear friend Sue. She’s a former children’s librarian who is now a stay-at-home mom and volunteer for practically anything you can imagine. She’s incredibly creative and pretty much does everything with a wonderful, unmistakable flourish.

A few years back, she decided to host a bash for some of her family and friends. Fun! Of course, it could be no ordinary party. Sue decreed that it would be a chili cook-off. Double-fun!

Weeks ahead of the party she whispered to me news of a special entry … the legendary Crazy Pineapple Chili from her brother-in-law, Gary. Sue reported that this chili had won all manner of cook-offs and friendly little competitions.

I anxiously awaited my meeting with this chili for weeks. I wasn’t disappointed.

IT WAS AMAZING! (Oh – and Sue’s bash was fab, too, of course! 😀 )

But really … this chili …

Despite there being some other great chilis at Sue’s party that night, this uniquely delicious chili certainly won the day. Hands-down, over-the-top, exceeding-my-expectations.

Crock-Pot Crazy Pineapple Chili Recipe {}

It’s rich and tomato-y, with wonderful flavor from Italian sausage (surprise again – no ordinary hamburger in this chili, my friends!). And then the pineapple … so, so good. It lends a warm, luscious sweetness that perfectly counterpoints the savory and spicy notes.

It’s an epiphany in a bowl.


Since Sue’s party, it’s gone on to win again, as expected. Most recently, it won my neighborhood’s chili cook-off. I was so bummed that my family had a conflict (ummmm … too many soccer games … you know). ‘Cause you know what chili I wanted to make, right?!?! But then I was thrilled to hear that this chili DID make an appearance (and won the grand prize, none-the-less)! It was entered by another dear friend, Lisa, who’s also been head-over-heels in love with it ever since Sue’s party!

You see what I mean. It kinda develops a loyal following.

Crock-Pot Crazy Pineapple Chili Recipe {}Know what you’re gonna love even more than how great it tastes, though?


Crock-Pot Crazy Pineapple Chili Recipe {}We’re talking crock-pot cookin’, my friends! You can even cook the sausage and onions the night before and refrigerate, so it’s extra-quick to throw everything together in your slow cooker in the morning. Or, you can make the chili ahead and freeze it in batches. So simple!

Now as you would absolutely expect from THK, we tinkered with Gary’s recipe a little. Because it wasn’t amazing? No … it’s all kinds of amazing, for sure. We made just a few adjustments to quell the heat a bit for the kiddos (but don’t worry – our recipe card has suggestions for amping the heat right on back up!).

We also slashed some of the fat. A simple swap that no one will ever notice is using Italian turkey sausage instead of regular, full-fat Italian pork sausage.

Crock-Pot Crazy Pineapple Chili Recipe {}Next, we traded out some of the sausage for black beans. They add great texture and loads of nutritional benefits.

Not a bean fan? Or maybe you live in Texas, where putting beans in chili is practically a jailable offense? No worries – you can leave those beans out altogether or even swap back in a bit more sausage, just like in Gary’s original recipe.

Here at THK, we’ve made it both ways and can never get people to agree on the beans vs. no beans debate. But then, that’s pretty much the story of all chilis – the beans are always the conundrum.

So make it our way … make it your way … make it any way. You’d be CRAZY not to!

Crock-Pot Crazy Pineapple Chili

Crock-Pot Crazy Pineapple Chili

Yield: About 10 cups
Prep Time: 10 minutes
Cook Time: 4 hours
Total Time: 4 hours 10 minutes

Contest-winning chili with an amazing flavor twist that people go crazy over! Quick and easy in the slow cooker – and healthy, too! Keep it on the mild, slightly sweet side, or use our tips to spice it up!

  Freezable  •  Make Ahead    Gluten Free  


  • 20 ounces sweet Italian turkey sausage (bulk, or links with casings removed)
  • 1 medium onion, chopped to equal about 2 cups
  • 1 (20-ounce) can pineapple tidbits in juice (divided)
  • 2 (28-ounce) cans seasoned diced tomatoes (such as Dei Fratelli)
  • 1 (15-ounce) can black beans, rinsed and drained
  • 1 (6-ounce) can tomato paste
  • 1 1/2 tablespoons chili powder
  • 4 teaspoons ground cumin
  • 2 cloves garlic, minced
  • shredded reduced-fat cheese, reduced-fat sour cream and hot sauce (such as Tapatío) for serving, if desired


  1. In a non-stick skillet over medium heat, cook sausage and onions, stirring to crumble sausage. Once sausage is cooked through, drain off any fat and transfer the sausage and onions to your slow cooker.
  2. Drain the pineapple, reserving both the juice and the fruit separately. Add the juice to the slow cooker. Cover and store the fruit in the refrigerator (it will be added toward the end of cooking).
  3. Add tomatoes, black beans, tomato paste, chili powder, cumin and garlic to the slow cooker.
  4. Stir everything to combine.
  5. Cook on low (6-8 hours), adding reserved pineapple during last hour or two of cooking, or on high (4-5 hours), adding pineapple during last 1/2 hour - hour of cooking.
  6. Serve topped with cheese, sour cream and hot sauce, if desired.


Pineapple: The texture of the cooked pineapple is completely controlled by when you add it. We prefer to add it toward the end of the cooking time, so that it's still fairly firm. If you prefer it to be more melded into the chili or you simply won't be able to add it toward the end of cooking, then you can toss it in at the beginning – it will be cooked down and much less pronounced in texture, but still very good.

Beans or no beans: If you don't want beans in your chili, you may certainly leave them out, and can also increase the amount of meat. We love the texture and the health benefits of the beans, but feel free to try it different ways!

Spice: This recipe is intentionally fairly mild and kid-friendly. If you'd like more spice, you can increase the chili powder and/or sub in spicy Italian turkey sausage. Perhaps the best way to make it versatile for different pallets, though, is simply to pass hot sauce at the table so everyone can season to taste.

Make-ahead: You can prepare the meat and onions the evening before, and then refrigerate until you assemble your ingredients in the slow cooker. You can also make the chili entirely in advance and freeze it in large batches.

Nutrition Information:
Yield: 10 servings Serving Size: 1 cup
Amount Per Serving: Calories: 469Total Fat: 8gSaturated Fat: 1gTrans Fat: 0gUnsaturated Fat: 4gSodium: 626mgFiber: 15gProtein: 22g

Nutrition information should be considered an estimate only, and may vary depending on your choice of ingredients or preparation. No guarantees are made regarding allergies or dietary needs. Always consult a physician or dietician for specific advice and questions.

Did You Make This Recipe?

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Crock-Pot Crazy Pineapple Chili Recipe {}
Crock-Pot Crazy Pineapple Chili Recipe {}

137 thoughts on “Crock-Pot Crazy Pineapple Chili”

    • Hi there! Apologies for the delay in responding – I’m out of the office on vacation this week. Hope it’s not too late to help you. I’ve never tested this chili recipe on the stovetop, to be able to specify exact timing, etc. But I’m sure that it can also work out fine. Good luck – and let me know how it goes! ~Shelley

  1. Made this for a chili cook off with an alternative category – it won, and rightfully so, it’s tasty. I made a batch and a half and for the half used sweet Italian pork sausage. I kept the pineapple out until the end, but sprinkled the pineapple with chipotle powder while it sat to give it a zing. People were surprised, it is delicious, will make again.

    • Congratulations on the win, Nate – I’m so, so happy this recipe was a winner for you, just as it has been at so many other chili cook off competitions! And I love the tip of adding chipotle powder for people who’d like to amp up the “zing” – thanks for sharing your great suggestion, and for the lovely feedback! 😀 ~Shelley


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