Crock-Pot Crazy Pineapple Chili

~ 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!

THK By Shelley

We’d Love to Hear From You!

Have you ever entered a cook-off? Been a taste-tester? Tell us … what was the winning dish?

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Crock-Pot Crazy Pineapple Chili

Preparation 10 min. 2017-08-17T00:10:00+00:00 Cook Time 4-8 hours 2017-08-17T00:00:00+00:00
Serves About 10 cups     adjust servings


  • 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 ½ hour - hour of cooking.
  6. Serve topped with cheese, sour cream and hot sauce, if desired.


Recipe Notes

Pineapple: The texture of the cooked pineapple is completely controlled by when you add it. We prefer to add it toward the end of 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.

We'd love to see your photos of this recipe! Follow us on Instagram, Facebook, Pinterest and Twitter and tag @TwoHealthyKitchens!


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


Crock-Pot Crazy Pineapple Chili — 76 Comments

    • Hi there, Rachel! First off – I just really want to apologize for the delay in responding to your question. I’m going back through the many questions and comments we received from readers over the holidays, making sure we didn’t miss any, and I’m so sorry that I found yours and hadn’t gotten back to you more quickly! At any rate, I have a couple of thoughts that might help. First off, you could simply try leaving out the beans altogether. The chili will be a bit more soupy, but I think it will still be delicious for you. If you’d like to increase the meat, though (although this will also increase other things like fat and calories), I would suggest trying about 8-12 additional ounces to make up for the bulk of the beans you’ll be leaving out. This will, of course, also somewhat increase the spices that are inherent in the sausage, so the Italian seasonings or (if you’re choosing to use spicy Italian turkey sausage) the spiciness, will increase along with the added meat. If you find that to be a problem, to avoid that, one other option might be to try adding regular ground turkey meat to replace the beans, instead of additional Italian turkey sausage. I hope those ideas help, and that I wasn’t too late to be of assistance! Have a wonderful weekend! ~Shelley

  1. HI – I am looking to double the recipe, what are your thoughts on this? Would I need to change anything? increase cooking times, etc? – Thanks so much!

    • I think this chili will easily double, with no problem. Just make sure your slow cooker is plenty big enough to hold such a large batch (slow cookers generally work best when they’re about 3/4 full, but you can check the manual on your specific model to see exactly what it recommends). The only change I can think of is that you might possibly want to plan to allow a little extra cooking time, especially if your slow cooker is overly full, but since the meat is fully cooked before you add it to the crock-pot, that wouldn’t be so much of a food safety issue as simply an issue with making sure the onions are cooked to a nice texture and all the flavors have plenty of time to mingle and meld. Good luck – and thanks for the question! 🙂 ~Shelley

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  4. I won our chili cook off last year with a non traditional chicken chili and have been goaded about it all year (they tease it was a chowder), so I knew I had to find a super special recipe for this year to silence them! I have it all in the crockot now, wish me luck!!!! Just hoping no one else found this recipe lol

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  6. I think I am going to enjoy the pineapple in this chili. A great flavor twist!! Cooking never gets better than when a crock-pot is involved!!

    • The pineapple really is such an unexpectedly awesome twist! Sometimes people are a bit suspicious … until they try it, and then they’re so totally hooked! And yup – I’m with you on the crock-pot thing … absolute life-saver on busy nights! 😀 ~S

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  8. I recently won a chili cook off and was searching for next year’s recipe. I think this is it! Do the tomato chunks cook down?

    • Thanks, Michelle! I love awesomely unique, creative flavor twists, too – that’s why I was so intrigued by this chili recipe, before I’d ever even gotten to taste it! I think you phrased it perfectly – it’s just the right balance of sweet and bold flavors. Oh my goodness, I haven’t made this chili recipe in a while, and thinking about it as I type this makes me want to run right off and get some cookin’ ASAP! Yum! Can’t wait for you to try it! Thanks so much for stopping by! 😀 ~Shelley

  9. I am entering this chili in our churches Super Bowl party and we are making a second batch for dinner tonight!

    Does anyone know the calories in this?

  10. Chili cook off for the Super Bowl party and well….. I want to win. My boring plain chili variation I think wouldn’t stand out so I went to the Internet to see what’s out there. Came across this post and was intrigued to say the least. Looking for something different that will stand out from the rest. I think I found it! I’ll let you know how it goes. Shopping for the ingredients tomorrow and hoping for the best. Post up the result afterwards. Excited to try this out and hopefully a win to boot.

    • I’m so excited for you to try this! My next-door neighbor’s slightly spicier version of this chili has seriously won my neighborhood’s cook-off two years running! Depending on who the audience/judges are at your cook-off – make sure you check out our tips for making this chili spicier/milder (you know – like maybe make it spicier for a bunch of rowdy men vs. for a family with little kids!). The spice level is totally controllable and a matter of preference, just like whether or not you include the beans. Play to your audience – and we hope you win the cook-off!!! Good luck!!!! 😀 ~Shelley

  11. This was a winner Saturday when we had friends for lunch. Kids and parents alike loved it – beans all the way! Thanks for another good one!

  12. I had a crazy morning and didn’t have time to put this on in the crock pot before work. Is there any way I can make this on the stove? My son has football practice and we’ve been dying to try this!

    • Hi, Nicole! I hope my response will reach you in time! I just came flying in the door myself, from my son’s soccer game – sounds like we’re having the same kind of night, huh!?!?

      Anyway – I honestly have never made this on the stovetop before, but it should translate ok for you. The only problem may be that the flavors won’t have as much time to meld and develop as they would over several hours in the slow cooker. But, on crazy-busy days, sometimes you’ve gotta make those kinds of compromises, right!?!?

      So here’s what I’d try: Proceed with step 1, as written. Then, once the meat and onions are cooked, add all the ingredients as specified in steps 2 and 3 into a big soup pot with the meat and onions. I would also go ahead and add the pineapple tidbits, rather than reserving them as you would for the slow cooker. Simmer as long as you have time for, to allow the flavors to develop – maybe 15 minutes, maybe 30 minutes … whatever you can manage. A little longer will be better, but do what you’ve gotta do to get dinner on the table!

      I hope this works all right and saves your evening!!! Good luck!!! 😀 ~Shelley

  13. AMAZING! I’m not sure if my wife followed the recipe exactly or not, but we just ate some amazingly good chili tonight for dinner and I found this website open on the computer. Coincidence, I think not. Pineapple Chili was super fantastic. Will definitely do this again. Thank you.

    • High-five on beans in the chili! (So nutritious, right?!?) This is insanely, surprisingly delicious! People are constantly shocked at how much they love the unique flavor profile. Even if they’re a little bit unsure if they’re going to like it … after that first bite, they’re completely hooked! Plus, it’ll be the perfect warm-you-up to get you through your Australian winter (trust us – if it can get us through Ohio’s winters, you’re covered for sure!! 😀 ). ~G&S

  14. Hi Gretchen and Shelley,

    I am making this today! I always add black beans to my chili but never pineapple. Thanks for sharing.

    • Mmmmmm … it really is! People are so surprised by how much they love such a unique flavor combination! And you can feel good knowing that you’re serving friends and family something that’s a bit lighter, a bit healthier (and loaded with nutritious fruit and veggies!) … while all they care about is how great it tastes! Everybody wins! 😀 ~G&S

  15. I tried your recipe —- and —- it’s tasty! Since we’ve had the original, we can make the comparison, and both Scott and I agree that your version tastes like Gary’s. I would add that it tastes lighter. Maybe that’s a strange adjective, but I think the turkey sausage lightens the chili up and prevents those “chili burps” later in the evening (LOL)! I have never used turkey sausage before, so thank you for the introduction. Your recipe is super-easy to make, and while Gary and my sister, Karen, pronounce that crazy pineapple chili should not contain beans, my family liked the addition. 🙂

    • Hi, Sue! We’re thrilled to have your expert feedback! Now, I have to admit that, knowing how Karen hates beans in her chili (which is kinda the whole reason Gary developed a bean-free chili for her in the first place), I knew they would be sticking to their guns and going with the beanless version! Perfect example of why we still included the beanless option (well, and for our Texan THK fans, too …). But, I’m so excited to hear how much you and Scott and your kiddos enjoyed our lighter version … and that you think it still retains the original flavor! That’s a huge compliment, and I’m so happy you took a moment to give us your feedback! Oh, and getting rid of those chili burps (total LOL :D)? You’re welcome! ~Shelley

    • Hi, Christine! Great timing on your comment, since I know you’re a vegan blogger! As I actually just mentioned in my reply comment to Kelly below (great minds must definitely think alike!), I do absolutely think that you could easily make a vegan (or vegetarian) version of this, as well. I’ve never tried it with this specific recipe, but I do think it would work. So glad you’re intrigued (I sure was when I first heard about it!) … hope you give it a go! 😀 ~Shelley

    • Thanks, Kelly! I’m sure you could vegan-ize this chili with vegan-friendly sausage or veggie crumbles. I actually love veggie crumbles (and use them often in a veggie soup we’re posting this fall), but I’ve never tried them specifically in this chili. I think they’d work just fine, though. You could also try simply leaving out the meat altogether and increasing the amount of beans (maybe use a second type of beans such as red kidney or cannellini for variety). Regardless, you’ll want to adjust the seasonings a bit to account for the fact that you’ve lost the Italian spices inherent in the sweet Italian sausage my version calls for. I would love to know how it goes if you try it! 😀 ~Shelley

  16. Yes, pineapple in chili…sounds delicious, I love the idea of sweet and tart flavors in chili…nice twist.
    Thanks for the recipe and hope you are having a wonderful week 😀

  17. Guess what I’m making TODAY on this cold weather calamity day off of school? Can’t wait to try it. Jen O. has won the EW Chili cook off 4 yrs in a row. I’m hoping to give her a run for her money. Miss you both tremendously!! Hugs to the kids from me.

    • You are most definitely going to reign supreme in the EW Chili Cook-Off this year … especially if you’ve got that sweet little helper on your side! 🙂 Oh! Maybe even make double batch and freeze some for those hectic evenings!

      Hmmmm … Do you happen to need taste-testers for this competition? We may be able to assist!

      Stay warm – looks like more cold to come! Hugs to you! ~G&S

  18. Great addition of the pineapple, it definitely changes the flavor of a traditional chili! I have never entered a cook-off, but my roommate was preparing for one yesterday.

    • Ohhhh … what was your roomie making?? How did it go? Was it the winning recipe??

      The pineapple definitely makes this chili unique! It adds that little something special that makes it totally stand out!

      Hmmm … maybe you should enter a cook-off! With this chili recipe!! 🙂 ~G&S

  19. I love chili!! So lovely this time of year! And what a great idea to add pineapple and mix things up a bit!! My mom makes a sweet chili that I love so much!! I bet yours was delicious!! Hope that you have a great week 🙂

    • Not sure about you … but we are about to experience another polar vortex! So yes … chili is EXACTLY the perfect thing to have this time of year!! We have certainly had our fill of extreme cold this winter, and chili recipe has kept our families full and warm! 🙂
      Yummmm … another sweet chili recipe! Wanna share?? 😉 ~G&S

  20. Pinneaple in chili??? Now, this sounds interesting to me! I think I’d love it, actually ; ) Thanks for the inspiration, girls. This is such a lovely idea that I’m eager to try!
    Hope you’re having a wonderful weekend!

    • Yes, Consuelo! Put the pineapple in the chili … you’ll be so happy you did! It just adds the perfect balance of sweet to the sausage and spices. Absolutely scrumptious!! We think you’ll love it, too! 😀 ~G&S

  21. I love the idea of hosting a chili cookoff….I will have to keep it in mind for next fall!! And this chili, well, I don’t think I’ll be able to wait that long to try it! Thanks for linking it up tonight at Saturday Night Fever!

    • Hi, Cathy! You should definitely try hosting a chili cook-off! It’s really such fun – everyone loves trying all the different recipes and debating the merits of each one. It’s an automatic conversation-starter and gets all the guests participating in the spirit of the party (even if they don’t know each other)! Mmmmmmm … but DEFINITELY try this chili before that! We’ve had some feedback already from FaceBook fans who’ve tried it and reported how much their families loved it! Give it a go for sure! 😀 ~Shelley

    • Yes Jess – we really hope you try this recipe! Especially with this brutally cold weather we’ve got right now, a pot of this chili is exactly what we all need! The blend of flavors are so unique and just plain good!! Enjoy! ~G&S

  22. We have a chili cook-off every year and my chili wins. But, I need to switch it up a bit…so I think this might be the perfect secret weapon for next time! They’ll be expecting to compete against my same ol’ chili, but then I’ll whip a new recipe on them and still win! Thanks Shelley! Looks fantastic! Pinned!

  23. I’m a Texas girl and I love beans in my chili! I love beans so much I couldn’t think of not adding them. I may be the only Texan who has never had true Texas Cowboy Chili. Just saying that makes me think of sitting around a campfire with a bowl of chili. Haha 😀 Now, this Chili may knock some of those cowboy off their feet! I’ve never had pineapple in chili, but it sounds like it would be quite tasty. I love that it is made in a crockpot! Awesome time-saver!!

    • I know – don’t you just love crock-pot recipes?!?! This chili is perfect for that method of cooking because the long, slow cook time really allows the wonderful flavors to come together. Plus … super-easy, hands-off cooking! 😀 Double-awesome! Giddy-up, cowboys! (Ummmm … do real Texans actually say that?!?!?) ~Shelley

    • Oh yeah! Perfect for a Super Bowl party! Any party actually – it’s great to feed a crowd! Just last weekend, I’d made a double batch ahead of time and frozen it all, then served it at my kiddos’ big family birthday party (they’re twins … so … same b-day!). Anyway, it was a smash hit, as always – perfect party food for a big group! 😀 ~Shelley

    • Yeah – this is seriously good stuff! As soon as you taste the pineapple in this chili, it’s one of those eureka moments when you wonder why you never tried this before! Well … after the first time you make it, it definitely won’t be the last! Enjoy! 😀 ~G&S

    • Thanks so much, Taylor! The slow cooker makes it incredibly easy, and it gives the flavors a chance to meld beautifully! I think you’ll be surprised at how gorgeous the flavors of pineapple and sausage are together, along with the other typical chili flavors. Yum! 😀 ~Shelley

  24. As you know, one of my family favs! I use hot Mexican chili powder and half of my sausage is hot/spicy. The result? It’s zippy without being too spicy. Hope everyone enjoys!

    • Hey, Lisa (aka The Neighborhood Chili Cook-Off Winner! :D)! Thanks for the tips on how you spice up your version! Three out of the four of us in my family would love the extra heat, but keeping it milder means that I win with FOUR out of the four of us! We just keep that Tapatío handy! So … at the next Neighborhood Chili Cook-Off … I guess you, Sue and I will all have to duke it out for who gets to bring the Crazy Pineapple Chili! Lol! Hugs … ~Shelley

    • Thanks, Lori! It really is so awesome – the pineapple is such a unique and delicious twist! People are really surprised by how much they love it! And yes – you know Gretchen and I are all about the healthy addition of the beans! Happily, even for people who don’t want to include the beans, this chili is still brimming with leaner meat, and loads of nutritional goodies from the onions, all those tomatoes, and the scrumptious pineapple! 😀 ~Shelley

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