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Cowboy Steak Chili

Cowboy Steak Chili

By: LalainePosted: 09/26/2017Updated: 06/29/2019

Cowboy Steak Chili with diced beef and tender beans in a smoky, chili-spiced tomato gravy is the ultimate chilly day food. Serve with cornbread for a hearty dinner or set out with various fixings for DIY game day eats!

Cowboy Steak Chili was my (successful) attempt to oust G as our resident chili master. Indeed his almost-famous 15-minute chili had quite a run in our house and no doubt it makes for an amazing dinner meal, especially on busy weeknights. It’s easy to prep and delivers the big, bold flavors we crave in minutes.

However, it was time for us to seriously up our chili game and go low and slow the way great chili should.

This cowboy steak chili definitely kicks things up with a few simple changes:

  • Instead of the quintessential ground beef, I used a hefty chunk of chuck roast which I hand-cut into about 1/4-inch pieces. The flavorful beef sure made for chili that’s chunky and meaty and absolutely delish!
  • In place of commercial chili powder, I used three types of dried chili peppers which I soaked and briefly pureed in the blender. The deep, rich flavors are definitely worth the extra effort! If you can’t find these dried chili peppers, substitute 2 tablespoons ancho chili powder or to taste.
  • I swapped homemade pinto and kidney beans for canned. I just happened to have some leftover from the charro beans I made for a fiesta party we had a few days ago so feel free to use canned beans for convenience. Although from-scratch beans seem to hold up better, they don’t really make a big difference in my opinion. Just rinse the canned beans well and add during the last hour or so of cooking to keep from turning into mush.

We love to top our chili with shredded cheddar and chopped onions but go ahead and load it up with sour cream, crushed tortilla chips, green onions, diced fresh tomatoes, sliced avocado, olives, and any of your favorite fixings.

Want a complete meal? Bake up a batch of these Sweet corn muffins or this jalapeno cornbread while your stew is simmering on the stove! They’re perfect for sopping up that thick, spicy tomato gravy!

Not only cowboy chili the ultimate comfort food to warm you up on chilly winter days, it makes for great game day fare as well.

Make a humongous batch, keep warm in the slow cooker on low, and set out little bowls with a variety of toppings. Your guests can DIY while you get to enjoy their company!

Did you make this? Be sure to leave a review below and tag me @OnionRingsAndThings on Facebook and Instagram!

Cowboy Steak Chili with diced beef and tender beans in a smoky, chili-spiced tomato gravy is the ultimate chilly day food. Serve with cornbread for a hearty dinner or set out with various fixings for DIY game day eats!

Prep Time: 10 mins

Cook Time: 2 hrs

Total Time: 2 hrs 10 mins

Author: Lalaine

Course: Appetizer, Main Entree

6 Servings


  • 2 dried ancho chiles
  • 2 dried California chiles
  • 3 dried chipotle chiles
  • 2 1/2 pounds chuck roast
  • 3 tablespoons canola oil
  • 4 cloves garlic, peeled and minced
  • 1 onion, peeled and chopped
  • 3 cups beef broth
  • 1 can (28 ounces) crushed tomatoes
  • 1 tablespoon cumin
  • 1 tablespoon brown sugar
  • 1 tablespoon salt
  • 1 can (14.5 ounces) kidney beans, drained and rinsed well
  • 1 can (14.5 ounces) pinto beans, drained and rinsed


  • In a small bowl, combine the dried ancho chiles, dried chipotle chiles, and enough boiling water to cover. Let stand for about 10 to 15 minutes or until softened.

  • Remove and discard the stems and seeds. Transfer the chiles to a blender and about 1/4 cups of the soaking liquid. Pulse a few times to a smooth paste.

  • Trim chuck roast of excess fat and cut into about 1/4 inch cubes. You should have about 2 pounds after trimming.

  • In a Dutch oven over medium-high heat, heat oil. Add beef and cook for about 2 to 3 minutes on each side or until lightly browned. Remove from pot and keep warm.

  • Lower heat to medium and add the remaining oil to pan as needed.

  •  Add onions and garlic and cook for about 2 to 3 minutes or until softened. 

  • Add beef broth and bring to a boil, scraping any browned bits on the bottom of the pot.

  • Return the beef to the pot including any juices. 

  • Add crushed tomatoes, pureed chiles, cumin, brown, sugar, and salt. Stir to combine.

  • Lower heat, cover, and simmer for about 2 hours or until meat is tender but not falling apart. If the chili is drying before the meat is tender, add more beef broth or water as needed.

  • Add pinto beans and kidney. Continue to simmer until sauce is thickened and reduced to about 2 cups.

  • Transfer to serving bowls and top with shredded cheddar and onions as desired. Serve hot.

Nutrition Information

Calories: 623kcal, Carbohydrates: 42g, Protein: 48g, Fat: 30g, Saturated Fat: 10g, Cholesterol: 130mg, Sodium: 2252mg, Potassium: 1555mg, Fiber: 13g, Sugar: 14g, Vitamin A: 3300IU, Vitamin C: 13.2mg, Calcium: 140mg, Iron: 8.5mg

“This website provides approximate nutrition information for convenience and as a courtesy only. Nutrition data is gathered primarily from the USDA Food Composition Database, whenever available, or otherwise other online calculators.”

About Lalaine

Welcome to Onion Rings and Things where you’ll find hundreds of comfort food recipes, crafts, and printables. Browse around and make something fun or tasty today! Read More

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