Quick Recipe Version (TL;DR)
Quick Ingredients
- 3 tbsp olive oil, divided
- 2 medium fennel bulbs, thinly sliced (fronds reserved)
- 1 large yellow onion, diced
- 4 cloves garlic, minced
- 1.5 lb mild or hot Italian sausage, casings removed
- 1 tsp fennel seeds, lightly crushed
- 2 tbsp chili powder
- 2 tsp ground cumin
- 1 tsp smoked paprika
- 1.5 tsp dried oregano
- 1/4 tsp cayenne pepper (optional)
- 2 tbsp tomato paste
- 1 (28 oz) can crushed tomatoes
- 3 cups low-sodium chicken broth
- 2 (15 oz) cans cannellini beans, drained and rinsed
- 1 bay leaf
- 1–2 tbsp red wine vinegar or balsamic vinegar
- Salt and black pepper, to taste
- Optional toppings: fennel fronds, parsley, Parmesan, sour cream
Do This
- 1. Prep fennel (reserve fronds), onion, and garlic; drain and rinse beans.
- 2. In a large pot, caramelize fennel and onion in 2 tbsp olive oil over medium heat, 15–20 minutes, until deep golden.
- 3. Add garlic, fennel seeds, chili powder, cumin, smoked paprika, oregano, and cayenne; cook 1–2 minutes.
- 4. Push vegetables to the sides, add 1 tbsp oil and sausage; brown well while crumbling, about 8–10 minutes.
- 5. Stir in tomato paste, cook 2 minutes, then add crushed tomatoes, broth, bay leaf, salt, and pepper; bring to a simmer.
- 6. Simmer gently, uncovered, 20–25 minutes; add beans and cook 10 more minutes. Adjust thickness with water or simmer to reduce.
- 7. Finish with vinegar, taste and adjust seasoning, then serve hot with toppings of choice.
Why You’ll Love This Recipe
- A cozy, hearty chili with a twist: sweet, caramelized fennel and classic Italian sausage.
- Perfect balance of sweet, smoky, and gently spicy flavors with creamy cannellini beans.
- One-pot comfort food that feels special enough for guests but easy enough for a weeknight.
- Flexible base recipe: adjust spice level, swap proteins, or make it more veggie-forward.
Grocery List
- Produce: 2 fennel bulbs, 1 large yellow onion, 4 cloves garlic, fresh parsley (optional), fresh fennel fronds (come with bulbs)
- Dairy: Parmesan cheese (for serving, optional), sour cream or plain Greek yogurt (optional)
- Pantry: Olive oil, chili powder, ground cumin, smoked paprika, dried oregano, cayenne pepper, fennel seeds, tomato paste, 1 (28 oz) can crushed tomatoes, 2 (15 oz) cans cannellini beans, low-sodium chicken broth, bay leaf, red wine vinegar or balsamic vinegar, salt, black pepper
- Meat: 1.5 lb Italian sausage (mild or hot, pork or turkey)
Full Ingredients
Chili Base
- 3 tbsp olive oil, divided
- 2 medium fennel bulbs, stalks and fronds separated; bulbs cored and thinly sliced (about 4 cups packed)
- 1 large yellow onion, diced (about 2 cups)
- 4 cloves garlic, minced
- 1.5 lb Italian sausage, casings removed (mild or hot; pork or turkey)
- 2 tbsp tomato paste
- 1 (28 oz) can crushed tomatoes
- 3 cups low-sodium chicken broth (or vegetable broth)
- 2 (15 oz) cans cannellini beans, drained and rinsed
- 1 bay leaf
- 1–2 tbsp red wine vinegar or balsamic vinegar (to finish)
- Salt and freshly ground black pepper, to taste
Spice & Aromatic Blend
- 1 tsp fennel seeds, lightly crushed
- 2 tbsp chili powder
- 2 tsp ground cumin
- 1 tsp smoked paprika
- 1.5 tsp dried oregano
- 1/4 tsp cayenne pepper (optional, for extra heat)
Optional Toppings & Sides
- Reserved fennel fronds, finely chopped
- Fresh parsley, chopped
- Freshly grated or shaved Parmesan cheese
- Sour cream or plain Greek yogurt
- Crusty bread, garlic bread, or cooked rice/polenta for serving
Step-by-Step Instructions
Step 1: Prep the fennel and aromatics
Trim the fennel bulbs by cutting off the stalks where they meet the bulb. Reserve some of the feathery green fronds for garnish and set aside. Cut the bulbs in half from top to bottom, remove the tough core, and thinly slice the fennel into half-moons. You want fairly thin slices so they caramelize nicely.
Dice the onion and mince the garlic. Drain and rinse the cannellini beans in a colander and let them sit to dry a bit. Remove the casings from the sausage if needed. Lightly crush the fennel seeds with a mortar and pestle or the back of a spoon to release their aroma.
Step 2: Slowly caramelize the fennel and onion
In a large, heavy-bottomed pot or Dutch oven, heat 2 tbsp olive oil over medium heat. Add the sliced fennel and diced onion, along with 1/2 tsp salt. Stir to coat everything in oil, then spread into an even layer. Cook, stirring every few minutes, for 15–20 minutes, lowering the heat slightly if the vegetables start to scorch.
You are aiming for a deep golden color and sweet aroma, not burning. The fennel and onion will soften, shrink, and gradually develop browned edges. This slow caramelization is what brings out the fennel’s natural sweetness and creates a rich base for the chili.
Step 3: Bloom the spices
When the fennel and onion are deeply golden, add the minced garlic, crushed fennel seeds, chili powder, cumin, smoked paprika, dried oregano, and cayenne (if using). Stir well to coat the vegetables in the spices.
Cook for 1–2 minutes, stirring constantly. This step, called blooming, wakes up the dried spices and infuses the oil with flavor. If the pot looks dry, you can add another 1 tsp of olive oil to help the spices toast gently without burning. You should start to smell a warm, fragrant, slightly smoky aroma.
Step 4: Brown the sausage
Push the fennel and onion mixture to the edges of the pot, creating a space in the center. Add the remaining 1 tbsp olive oil to the center and crumble in the sausage.
Cook the sausage over medium to medium-high heat for 8–10 minutes, breaking it up with a spoon or spatula into bite-sized pieces. Let it sit undisturbed for a minute at a time so it can brown and develop flavor before stirring again. Once the sausage is no longer pink and has some nicely browned bits, stir the vegetables and sausage together, scraping up any browned bits from the bottom of the pot.
Step 5: Build the chili base
Stir in the tomato paste and cook for about 2 minutes, stirring frequently, until it darkens slightly in color and coats the sausage and vegetables. This concentrates the tomato flavor and adds depth.
Add the crushed tomatoes, chicken broth, bay leaf, 1 tsp salt, and about 1/2 tsp black pepper. Stir well, scraping the bottom of the pot to loosen any stuck bits. Increase the heat to bring the mixture just up to a boil, then immediately reduce to a gentle simmer.
Simmer uncovered for 20–25 minutes, stirring occasionally. The chili will slightly thicken and the flavors will start to meld. Adjust the heat as needed to maintain a steady but soft bubbling.
Step 6: Add the beans and finish seasoning
After the initial simmer, add the rinsed cannellini beans. Stir to combine and continue to simmer uncovered for another 10–15 minutes. The beans should be very tender and the chili should have a thick but spoonable consistency.
If it seems too thick, add a splash of water or broth. If it feels too thin, simmer a bit longer to reduce. Remove the bay leaf. Stir in 1 tbsp red wine vinegar or balsamic vinegar, then taste. Add more vinegar if you want a brighter finish, and adjust salt and pepper as needed. The chili should taste balanced: savory, a little sweet from the fennel, with a gentle heat and a clean, slightly tangy finish.
Step 7: Serve and garnish
Finely chop some of the reserved fennel fronds and a bit of fresh parsley. Ladle the hot chili into bowls. Garnish each bowl with a sprinkle of fennel fronds and parsley, a generous grating of Parmesan, and a small dollop of sour cream or Greek yogurt if you like creaminess.
Serve with crusty bread, garlic bread, or over rice or polenta for an extra-hearty meal. The flavors will deepen even more as the chili sits, so leftovers are especially good.
Pro Tips
- Do not rush the fennel. The caramelization step is where a lot of the depth comes from. Keep the heat moderate and give it the full 15–20 minutes.
- Crush the fennel seeds. Lightly crushing them releases their oils and boosts the anise flavor that pairs so well with sausage.
- Brown the sausage properly. Let it sit in contact with the pan to get those flavorful browned bits instead of stirring constantly.
- Adjust thickness to taste. A few extra minutes of simmering will thicken the chili; a splash of broth will loosen it if it gets too dense.
- Make it your heat level. Use mild sausage and skip the cayenne for a gentle chili, or use hot sausage and extra cayenne for more kick.
Variations
- Lighter turkey version: Use turkey Italian sausage and low-sodium broth. The caramelized fennel still brings richness, so you will not miss the extra fat.
- Extra-veg option: Add 1 diced red bell pepper and 1 diced carrot to the pot along with the fennel and onion for more color and sweetness.
- Hearty vegetarian twist: Skip the sausage, use vegetable broth, and add an extra can of beans (such as chickpeas) plus 1 tsp more smoked paprika to keep the chili robust and smoky.
Storage & Make-Ahead
Let the chili cool to room temperature, then transfer to airtight containers. Refrigerate for up to 4 days. Reheat gently on the stovetop over low to medium heat, adding a splash of water or broth if it has thickened too much. This chili freezes very well: portion into freezer-safe containers, leaving a little headspace, and freeze for up to 3 months. Thaw overnight in the refrigerator before reheating. The flavors actually improve after a day, so this is a great make-ahead meal for busy weeks or entertaining.
Nutrition (per serving)
Approximate values per serving (1/6 of recipe, without toppings): about 480 calories; 26 g protein; 26 g fat (8 g saturated); 34 g carbohydrates; 9 g fiber; 7 g sugar; 980 mg sodium (will vary based on broth, sausage, and added salt). Using turkey sausage and low-sodium broth will reduce fat and sodium.
