• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
Cooking On The Weekends
  • About
    • Press
    • Contact
  • Recipe Index
  • "How To"
  • Work with Me
menu icon
go to homepage
  • About
    • Contact
  • Recipe Index
  • Subscribe
  • Shop
    • Facebook
    • Instagram
    • Pinterest
  • subscribe
    search icon
    Homepage link
    • About
      • Contact
    • Recipe Index
    • Subscribe
    • Shop
    • Facebook
    • Instagram
    • Pinterest
  • ×
    Home » Main Courses » Soups & Stews » Brisket Chili with Bacon and Chipotles

    Brisket Chili with Bacon and Chipotles

    Sep 6, 2015 · by Valentina · 30 Comments

    This post may contain affiliate links.

    Jump to Recipe

    Brisket Chili with Bacon and Chipotles is full of delicious, deep, rich flavors that will warm you to your soul. It's not just a comforting weeknight meal, you will totally wow weekend guests with it, too!Colorful striped bowl of brisket chili with fresh green herbs and chopped red onion on top.
    I love making recipes likes this brisket chili — layers and layers of flavors, each one building upon the last.

    The flavors are deep and complex . . . and when they're combined, they are exquisite.

    Make a double batch and have it for lunches or dinners during the week!

    Brisket Chili Recipe in a brightly colored striped bowl, topped with fresh herbs and chopped red onion.

    The Ingredients

    • brisket - When purchasing, choose a high quality ("choice") brisket, with an even layer of fat on one side and that's as equal in thickness along all sides as possible.
    • bacon - I love the flavor of applewood smoked bacon, though any bacon you like will be great.
    • onion - Try to choose onions that are firm, heavy for their size and without bruises.
    • garlic - Look for firm heads of garlic without any soft spots or green shoots, which is an indication of old garlic. Raw garlic cloves should be firm without any dark spots.
    • jalapeño pepper - A good pepper should be firm, deeply colored and slightly shiny.
    • chipotle peppers in adobo sauce - Chipotle Peppers in Adobo Sauce are jalapeño chiles that have been dried, smoked and packed in a sauce made of tomatoes and spices. They come in a can and you should be able to find it in any major grocery stores.
    • fresh oregano
    • dried oregano
    • ground cumin
    • chili powder
    • ground cinnamon
    • fresh tomatoes - Color and feel are the best cues to ripeness when selecting tomatoes. Ripe tomatoes should be slightly firm, with a little bit of give when gently squeezed, and they should have a deep red color.
    • dry red wine - Such as Merlot, Pinot Noir, Shiraz.
    • fresh corn - Choose corn with bright green husks that are wrapped tightly against the corn.
    • red kidney beans - Canned kidney beans are great for this.
    • bittersweet chocolate - This is the "secret ingredient" in my brisket chili. It adds richness, flavor and a creamy texture to the sauce.
    • salt - I cook with Kosher salt. It’s coarse and salts foods in a subtle way that enhances their flavor without making them taste salty.
    • black pepper - Preferably freshly ground.
    • optional garnishes: sour cream, grated cheddar, red onion.

    How to Make it

    - Preheat the oven to 225°F, and lightly coat a large oven safe skillet with olive oil. Season the meat with salt and pepper and place it -- fat side up -- in the pan. Cover it with a fitted lid or foil. Place it in the oven for 6 hours. Remove it from the pan let it cool slightly on a plate or cutting board. (Leave any grease and juices in the pan!)

    Cooked brisket being sliced against the grain.

    - Use the back of a knife or a spoon to gently scrape off the fat and discard it. Shred the meat with your fingers, or cut it into slices -- against the grain, and then into bite-sized pieces. Set aside.

    - Place the unwashed pan over medium-high heat and add the bacon. Stirring occasionally, cook until golden and mostly crispy. Add the onions, garlic and jalapeños and cook until the onions are soft and beginning to caramelize.

    - Stir in the chipotle peppers in adobo sauce, fresh oregano, dried oregano, cumin, chili powder, and cinnamon. Season lightly with salt and then turn the heat to the lowest setting.

    - Roughly chop the tomatoes or us a blender quickly until they're a coarse purée. Add this to the pan with the wine, turn the heat back up and bring to a boil. Then reduce the heat to low and let this simmer for at least 15 minutes.

    - Cut the kernels off the ears of corn and add them to the pan with the kidney beans and the prepared brisket. Keeping the heat low, simmer for another 20 minutes.

    Brisket Chili with bacon and chipotles in a cast iron skillet.

    - Add the chocolate and season to taste with salt and pepper.

    Recipe Tips and Substitutions

    • To save time for this recipe, you instead of fresh, you can use frozen and thawed corn, pre-minced garlic from a jar, only the dried oregano with an additional tablespoon of it, and canned, diced tomatoes.
    • You should make the brisket the day before you want to make the chili.
    Brisket Chili recipe in a pretty, red, yellow, orange and green striped bowl with fresh oregano, red onion and cheddar cheese.

    Can you make it ahead?

    Yes! Like most one pot meals, brisket chili will only get better with time. You can make it up to five days ahead. Reheat it on the stove when you’re ready to serve.

    Serving Suggestions

    Any of the following options would be fantastic with it . . .

    • Skillet Jalapeño Cornbread {Gluten-Free Recipe}
    • Smoky Hatch Chile Cornbread Casserole
    • Fried Meyer Lemon Caesar Salad
    • Herbed Garlic Bread
    • Hot Water Cornbread

    More Must-Try Chili Recipes

    • Roasted Butternut Squash Chili
    • Mexican Chocolate Chili

    This is an an ideal fall and winter comfort food, so keep the recipe close as the days cool down.

    Chocolate Chipotle Bacon Brisket Chili in a rainbow striped bowl

    Brisket Chili Recipe

    Valentina K. Wein
    This is an unbelievably flavorful chili that's rich, smoky, hearty and super delicious!
    Please note that the active work time for this recipe is 45 minutes, the remainder of the time is for the brisket to slowly cook -- and this can be done a day ahead of time.
    5 from 3 votes
    Print
    Prep Time 20 minutes mins
    Cook Time 6 hours hrs 25 minutes mins
    Total Time 6 hours hrs 45 minutes mins
    Course Main Course
    Cuisine American
    Servings 6 to 8
    Calories 444 kcal

    Ingredients
      

    • 2 pound brisket
    • 6 strips bacon, cut into bite-sized pieces
    • 2 cups yellow onion, small dice
    • 2 tablespoons fresh garlic, crushed, roughly chopped
    • 2 tablespoons jalapeño pepper, minced
    • 2½ tablespoons chipotle peppers in adobo sauce, roughly chopped
    • ¼ cup fresh oregano, finely chopped
    • 1 teaspoon dried oregano
    • 1 tablespoon ground cumin
    • 1 tablespoon chili powder
    • 1 teaspoon ground cinnamon
    • 2¼ pounds vine-ripened tomatoes
    • ½ cup dry red wine (such as Merlot, Pinot Noir, Shiraz)
    • 3 ears fresh corn
    • 2 (15-ounce) cans Red Kidney Beans, drained
    • 3 tablespoons finely chopped bittersweet chocolate
    • salt and freshly ground black pepper
    • optional garnishes: sour cream, grated cheddar, red onion

    Instructions
     

    • * YOU CAN DO THIS ENTIRE STEP THE DAY BEFORE -- JUST DON'T WASH THE PAN IF YOU DO. COVER IT WITH FOIL, KEEPING IT AS IS.*
      Prepare the brisket. Preheat the oven to 225°F, and lightly coat your largest oven safe skillet (cast iron is perfect) with olive oil. (See notes) Season both sides of the meat generously with salt and pepper, and then place it -- fat side up -- in the pan, and cover it with a fitted lid or heavy-duty foil. Place it in the preheated oven for 6 hours. Remove the brisket from the oven, and place it on a large plate. (Leave any grease and juices in the pan!) Let the brisket cool slightly, and then use the back of a knife or a spoon to gently scrape off the fat and discard it. Now either shred the meat with your fingers, or cut it into slices -- against the grain, and then into bite-sized pieces. (The bite-sized pieces will ultimately shred later in the recipe.) Set aside.
    • Cook bacon, onion, garlic and peppers. Place the unwashed pan over medium-high heat and add the bacon. Stirring occasionally, cook until golden and mostly crispy, about 5 minutes. Add the onions, garlic and jalapeños, still stirring from time to time, cook until the onions are soft and beginning to caramelize, about 15 minutes.
    • Add chipotles and spices. Stir in the chipotle peppers in adobo sauce, fresh oregano, dried oregano, cumin, chili powder, and cinnamon. Cook until this is very aromatic, about 2 minutes. Season lightly with salt and then turn the heat to the lowest setting.
    • Add tomatoes and wine. Either crush the tomatoes in a blender, or roughly chop them until they're a coarse purée. Add this to the pan, along with the wine, turn the heat back up to medium-high and bring to a boil. Then reduce the heat to low and let this simmer for at least 15 minutes -- the alcohol should be cooked off and the liquid should be beginning to thicken.
    • Prep and add the corn with the beans and brisket. Cut the kernels off the ears of corn and add them to the pan with the kidney beans and the prepared brisket. Keeping the heat low, let all of the flavors marry for another 20 minutes or so.
    • Add chocolate, season and serve. Mix in the chocolate and let it melt. Then season to taste with salt and pepper, and serve with any of the desired garnishes.

    NOTES

    My cast iron skillet is very large (12 inch), and I can make this entire recipe in it, from start to finish. If that's not the case for you, simply change to a larger pan when you need to -- ideally after the tomatoes and wine have simmered.
    Calorie count is only an estimate.

    NUTRITION

    Calories: 444kcal
    Keywords best beef stew recipes, comfort food recipes for fall and winter
    Have you tried this recipe?I'd love to see it on Instagram! Tag me at @cookingontheweekends or leave a comment & rating below.

    Cooking On The Weekends is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com. 

    More Soups & Stews

    • Cold Cucumber Soup with a slice of lemon in orange bowl with white rim
      Cold Cucumber Basil Soup
    • Italian yellow-edged bowl full with chicken and rice soup with carrot slices.
      Hearty Chicken Vegetable and Rice Soup
    • Chocolate Chipotle Colorado Style Chili in a ceramic golden bowl with cheese and cilantro on top.
      Mexican Chocolate Chili and Casa Mia Restaurant
    • 3 bowls of butternut squash chili with fresh oregano sprigs
      Butternut Squash Chili

    Reader Interactions

    Comments

    1. Sippitysup

      September 10, 2015 at 9:19 am

      I must give brisket in chili a go. It sounds so rich and delicious. GREG

      Reply
      • valentina

        September 10, 2015 at 11:13 am

        Rich and delicious it is. Especially with the bacon! 🙂

        Reply
    2. David

      September 12, 2015 at 2:20 pm

      I love the mole aspect of this chili! Brisket makes the best chili - used so much for that here in Arizona. The layers of love and flavor you have added make this darned appealing, even in the hot summer days!

      Reply
      • valentina

        September 12, 2015 at 2:41 pm

        Thanks, David. I know, it's still super hot here also (though cooler, I'm sure). I can't wait until it's cool enough for this sort of food every night. My favorite! xo Valentina

        Reply
    3. Judy @ ImBoredLetsGo

      September 13, 2015 at 6:16 am

      I'm always so intimidated with brisket but I think I'll get over that with this recipe. It sounds AWESOME. Pinning this!

      Reply
      • valentina

        September 13, 2015 at 9:19 am

        Thanks, Judy! Making the brisket is super easy. Hope you try and enjoy! 🙂

        Reply
    4. Kari

      September 13, 2015 at 7:04 am

      I've made spicy chocolate chili but never thought to add brisket and bacon - will have to try this out!

      Reply
      • valentina

        September 13, 2015 at 9:25 am

        Hope you like it Kari! 🙂

        Reply
    5. jen

      September 13, 2015 at 9:08 am

      I'm always looking for new chili recipes - this looks fantastic. Can't wait to try it

      Reply
      • valentina

        September 13, 2015 at 9:25 am

        Thanks, Jen! 🙂

        Reply
    6. evan kristine

      September 13, 2015 at 11:02 am

      i love this! i will defenitely try this, perfect with rice or taco's!

      Reply
      • valentina

        September 13, 2015 at 11:38 am

        Oh, I'd love it in a taco! Great idea!

        Reply
    7. Taylor | Perpetually Hungry

      September 14, 2015 at 7:23 am

      This chili looks SO good - makes me crave fall-weather. So ready to make stews and soups like this! Yum!

      Reply
      • valentina

        September 14, 2015 at 12:41 pm

        Thanks, Taylor! I know, I'm craving rain and clouds as much as this chili. 😉

        Reply
    8. Chris @ SimpleFood365

      September 14, 2015 at 9:34 am

      I have had a lot of different chili's over the years but never one with brisket. That sounds yummy!

      Reply
      • valentina

        September 14, 2015 at 12:42 pm

        This, Chris! Was the first time I used brisket and it was a big hit. 🙂

        Reply
      • Austin

        December 26, 2024 at 4:32 pm

        I made this recipe for a chili cook off between friends ( around 12 entries ) and took home first place. Thanks! It’s definitely delicious. I doctored up my brisket but everything else in the recipe is spot on

        Reply
        • Valentina

          December 27, 2024 at 1:10 pm

          Hi Austin. You made my day. This is fantastic. Happy you took home first place, and even happier it was so delicious! Happy Holidays, and Happy New Year. 🙂 ~Valentina

          Reply
    9. Molly Kumar

      September 14, 2015 at 11:05 pm

      This is such a comfortfood recipe - Delicious.

      Reply
      • valentina

        September 15, 2015 at 9:08 am

        Thanks, Molly. 🙂

        Reply
    10. Boastful Food

      October 28, 2015 at 5:03 pm

      I'm so glad your hubby eats meat again. This looks amazing!

      Reply
      • valentina

        October 28, 2015 at 10:29 pm

        Thanks, Raquel! 🙂

        Reply
    11. Blooper

      October 30, 2015 at 6:40 pm

      Hi there,

      Thanks for posting this; I'm making it right now. At what point do I put the brisket pieces back into the chili?

      Thanks!

      Reply
      • valentina

        October 31, 2015 at 1:58 pm

        5 stars
        Hi there. Oh I so hope I'm not too late and so sorry about the missing step! You'll see that step 6 has been edited -- that's where you add the prepared brisket. I hope all went well and that it was delicious!

        Reply
    12. Jerriann Fleming

      January 16, 2019 at 8:07 am

      5 stars
      I made this last night and it was more amazing than I could’ve imagined! Great in all this rain!!

      Reply
      • valentina

        January 16, 2019 at 8:36 am

        Hi Jeriann! So happy to hear from you. 🙂 Thank you for checking out my site and trying my recipe. So happy you loved this chili, and yes, perfect for these rainy days. Hello to everyone! ~Valentina

        Reply
    13. Marty

      October 13, 2019 at 7:00 am

      Could I substitute the wine for a bottle of chocolate stout beer instead? also it calls for 1/4 cup of fresh oregano? That seems like alot

      Reply
      • valentina

        October 13, 2019 at 9:58 am

        Hi Marty,
        I think the stout would be fantastic! That's a great idea! (I would use the same measurement as wine.) As for the oregano, it is a lot, but works well. Feel free to adjust it if you want -- it won't really affect the overall deliciousness of the chili. 😉 Enjoy and thanks for checking out my recipes. 🙂 ~Valentina

        Reply
    14. Kristy

      October 11, 2022 at 4:33 pm

      5 stars
      Oh My! Brisket AND bacon in the same chili recipe. This is definitely to die for. There is so much amazing stuff going on here with all the spices, peppers, wine, and of course the chocolate. A chili with tons of flavor and one that is perfect for the season. This is a must-have recipe for sure! Thanks, Valentina for sharing!

      Reply
      • valentina

        October 17, 2022 at 5:37 pm

        Thanks so much, Kristi! Enjoy and happy fall. 🙂 ~Valentina

        Reply

    Leave a Reply Cancel reply

    Your email address will not be published. Required fields are marked *

    Recipe Rating




    This site uses Akismet to reduce spam. Learn how your comment data is processed.

    Primary Sidebar

    Hi, I'm Valentina, certified chef, owner, recipe developer and photographer at Cooking on the Weekends. I'm also a mom of two boys and a Los Angeleno. I use seasonal whole foods to create unique and comforting recipes for casual entertaining.

    More about me →

    REFRESHING FROZEN DESSERTS

    • Cream-colored ceramic mug with coffee beans and a coffee popsicle sticking out of the top.
      Creamy Coffee Popsicles
    • Top view of Strawberry Swirl No-Churn Ice Cream in a small white mug with strawberry on top.
      Strawberry Swirl Ice Cream
    • Fat Free Cherry Frozen Yogurt in a cream colored bowl with a cherry on top
      Chocolate Frozen Yogurt with Cherries
    • Honey Grapefruit Popsicles on crushed ice with lemon leaves.
      Grapefruit Popsicle Recipe with Honey

    POPULAR SUMMER RECIPES

    • Open jar of lemon verbena pesto with small leaves on top.
      Lemon Verbena Pesto
    • Large ceramic serving bowl full with Watermelon Basil Salad with feta, avocado, and balsamic reduction.
      Watermelon Basil Salad with Avocado
    • Close up of Summer Fish Stew in black bowl.
      Summer Fish Stew with Cod
    • Several corn Ribs that are golden from roasting on a sheet pan
      Corn Riblets

    Footer

    ↑ back to top

    About

    • Privacy Policy
    • Press

    Newsletter

    Get new recipes you’ll love!

    Contact

    • Contact
    • Work with Me

    Review the privacy policy for Cooking on the Weekends

    Copyright © 2025 Cooking On The Weekends, All Rights Reserved