Portland's Best Chili [Updated 2025]

You know that feeling when the air starts to chill and all you crave is a hearty bowl of chili? Well, I’ve been on a mission to find the ultimate chili experience right here in Portland. After sampling creations from 12 top-notch spots, I’ve discovered some mouthwatering flavors that are sure to warm your soul and satisfy even the pickiest of palates.

Trust me, I take my chili seriously—I've tasted everything from classic recipes to daring twists that push the boundaries of flavor. So, whether you like it spicy, smoky, or topped with the perfect dollop of sour cream, I’ve got the inside scoop on where to find the best bowls in town. Let’s dive into this delicious journey together!

Flattop & Salamander

Highlights
Cute and clean establishment
Friendly and attentive staff
Delicious breakfast options
Small patio for outdoor seating
Short wait times for food

Flattop & Salamander: A Chili Adventure in Portland

Nestled in the heart of Portland, Flattop & Salamander is more than just a delightful eatery; it’s a charming oasis where chili takes center stage. As soon as I stepped inside, I was greeted by a cute and clean establishment that radiated a welcoming vibe. The friendly staff made me feel right at home, ensuring that my dining experience would be enjoyable from start to finish.

Now, let's get to the heart of the matter: the chili! I indulged in their signature bowl, and let me tell you, it was a flavor-packed journey. Each spoonful was a perfect blend of spices, with just the right amount of kick to make my taste buds dance.

While I patiently waited for my meal, I appreciated the short wait times—perfect for those with a busy schedule. Plus, the option to sit on their small patio was a fantastic way to soak in the Portland atmosphere.

If you’re searching for superb chili in a delightful atmosphere, Flattop & Salamander is a must-visit. Trust me, your palate will thank you!

You might also want to check out the best breakfast in Portland.

The Observatory

Highlights
Interesting menu options
Crispy, fluffy fries
Amazing biscuits and gravy
Fun atmosphere
Fantastic service

The moment I stepped into The Observatory, I could feel the vibrant energy that radiated from the eclectic decor and lively patrons. The atmosphere was inviting—perfect for a casual hangout with friends or a cozy solo visit. I was here for one thing and one thing only: the chili!

The Observatory offers an interesting menu that boasts a variety of options, but the chili truly stands out. This isn’t your run-of-the-mill bowl of beans and meat; it’s a delightful concoction that balances spices and flavors brilliantly. Each spoonful was a warm hug on a chilly Portland day, with just the right amount of heat that didn’t overpower but enhanced the experience.

Let’s not forget the crispy, fluffy fries served alongside. They perfectly complemented the richness of the chili, and if you’re feeling daring, the addition of melted cheese elevates the entire dish.

The fantastic service added to the delightful experience, with staff that were genuinely enthusiastic about the menu. If you’re searching for one of the best chilis in Portland, you owe it to yourself to swing by The Observatory. You might just discover your new favorite.

You might also want to check out the best sushi in Portland.

Portland Kettle

Highlights
Delicious homemade soups
Huge portion sizes
Excellent service
Friendly staff
Tasty pastrami sandwich

Portland Kettle is a hidden gem that definitely deserves a spotlight in the chili conversation! As I walked in, the inviting aroma of homemade soups enveloped me, making my mouth water in anticipation. I was thrilled to discover their chili was not just delicious, but served in huge portion sizes that could easily satisfy even the most ravenous appetite.

The friendly staff made the experience all the more enjoyable, exchanging banter while I perused the menu. They genuinely seemed to love their work, always eager to make recommendations. I opted to pair my chili with a tasty pastrami sandwich, and oh, what a combination! The richness of the chili paired wonderfully with the savory, tender pastrami, creating a fusion of flavors that danced on my palate.

But let us not forget the excellent service—the staff was attentive, ensuring my glass was never empty and my experience, nothing short of delightful. In a city brimming with culinary options, Portland Kettle stands out not only for its chili but for its welcoming atmosphere. If you're hunting for a little taste of comfort, this spot should be at the top of your list!

You might also want to check out the best steak in Portland.

Interurban

Highlights
Delightful elegance for dates
Excellent service and prices
Cool bar atmosphere
Quick food and drink service
Cozy patio with fire pit

Interurban: A Chili Lover’s Delight in Portland

On my quest for the best chili in Portland, I stumbled upon Interurban, a gem that effortlessly combines flavor with a cozy atmosphere. As soon as I walked in, I was greeted by a delightful elegance that felt perfect for a casual date or a friendly catch-up. The bar displays a cool vibe, inviting patrons to sip on creative cocktails while anticipating their hearty meal.

Now, let's talk chili. Interurban certainly knows how to make your taste buds dance! Their rendition is rich and robust, with a complex layering of spices that warms the soul. It's a comforting dish that feels just right on a chilly Portland evening.

The service was impressively quick without sacrificing attentiveness, making my dining experience all the more enjoyable. Plus, the reasonable pricing means I can indulge without breaking the bank! If the weather permits, be sure to snag a spot on their cozy patio with a fire pit—perfect for both ambiance and warmth.

In my opinion, Interurban blends taste and experience perfectly, making it a top contender on my chili tour. If you’re seeking a bowl that’s equally comforting and vibrant, this might just be your next favorite spot!

You might also want to check out the best italian restaurant in Portland.

Lawless Barbecue

Highlights
Friendly and attentive service
Clean and welcoming atmosphere
Less sweet BBQ flavor profile
Phenomenal brisket burger
Accommodating staff and orders

Lawless Barbecue in Portland is a true gem for chili enthusiasts and barbecue lovers alike. As I stepped into the inviting atmosphere, I was greeted by the friendly and attentive service that instantly made me feel at home. The space is not just clean, but has a vibrant aura that sets the perfect backdrop for enjoying comfort food.

Now, let’s talk chili. Lawless crafts a chili that is anything but cliché—it's robust and packed with flavor without being excessively sweet, thanks to their unique BBQ flavor profile. Each spoonful is a delightful dance of spices and tender meat, making it a standout in the Portland chili scene.

But wait, there’s more! The phenomenal brisket burger I couldn’t resist is a delightful sidekick to their chili. The accommodating staff were more than happy to customize my order, enhancing the experience.

In a city that takes its chili seriously, Lawless Barbecue truly steps up the game. Whether you're a chili aficionado or just someone looking to warm the soul, I wholeheartedly recommend making a pit stop here—it’s an experience that satisfies both the palate and the heart.

You might also want to check out the best brunch in Portland.

Cheryl's on 12th

Cheryl's on 12th is a hidden gem in the heart of Portland, boasting a chili that’s simply irresistible. The moment I took my first spoonful, the bold flavors danced on my palate, combining smoky undertones with a perfect kick of spice. Each bite is a warm hug on a chilly day! Topped with a sprinkle of cheese and a dollop of sour cream, it felt like comfort food elevated to an art form. The friendly ambiance and delightful service made my visit even more enjoyable. If you’re in search of chili that warms both heart and soul, Cheryl’s is a must-try!

You might also want to check out the best restaurant in Hillsboro.

Wolfs Head

When I stepped into Wolfs Head, the inviting aroma of spices hit me instantly. Their signature chili, a perfect balance of heat and heartiness, was a delightful surprise. I adored the unexpected twist of smoked paprika, which elevated the dish to new heights. Each spoonful offered a bold flavor profile, complemented by tender chunks of meat and vibrant beans. The cozy ambiance made it an inviting spot for a chilly day. Overall, Wolfs Head proves that Portland's chili scene is nothing short of fantastic, and I can't wait to return for another bowl!

You might also want to check out the best vegan restaurants in Portland.

Franks A Lot

Franks A Lot delivers a chili experience that's as bold as its name suggests! On my visit, I was captivated by the rich, smoky flavor profile that suggested each ingredient was chosen with care. The texture struck a perfect balance between hearty and smooth, allowing the spices to dance on my palate. Topped with a dollop of tangy sour cream and a sprinkle of chives, the presentation was delightful. The friendly staff added to the charm, making me feel right at home in this cozy eatery. If you’re in the mood for a satisfying bowl of comfort, look no further!

You might also want to check out the best pho in Portland.

Podnah's BBQ

At Podnah's BBQ, the chili is nothing short of a flavor explosion! Rich and hearty, it strikes the perfect balance between smoky and spicy. The generous chunks of meat mingle beautifully with the beans, while a hint of sweetness adds depth. As I savored each spoonful, the vibrant spices danced on my palate, creating a delightful, warm embrace. The cozy atmosphere perfectly complements this wonderful dish, making it a must-try for any chili lover. I left with a satisfied grin, already anticipating my next bowl. Podnah's BBQ truly elevates chili to a whole new level!

You might also want to check out the best ice cream in Portland.

Calle 21

At Calle 21, I was greeted by the tantalizing aroma of spices wafting through the air. Their chili, a delightful blend of bold flavors, features a smooth texture that warms you from the inside out. With a perfect balance of heat and heartiness, each spoonful was a dance of smoky and savory notes on my palate. The added flair of fresh garnishes provided a lovely crunch, elevating the experience even further. If you’re hunting for a chili that embraces both tradition and creativity, Calle 21 is a must-visit. Don't miss it; your taste buds will thank you!

You might also want to check out the best asian food in Portland.

Portland Burger

At Portland Burger, the chili is a delightful surprise that dances on the palate. With a rich and hearty base, it's boldly seasoned, elevating the classic recipe into something extraordinary. The generous chunks of beef melt perfectly alongside the beans, creating a harmonious blend. Pouring this hearty concoction over their freshly made fries is a game changer—it's indulgent and utterly satisfying. The ambiance is casual, making it a perfect spot for a laid-back meal. If you're on a quest for chili that packs a punch, Portland Burger is a must-try that may just become your new favorite!

You might also want to check out the best restaurants in Tigard.

Roake's on Columbia

Roake's on Columbia is a delightful gem where chili reigns supreme! Upon my first spoonful, I was immediately enchanted by the rich, velvety texture and a perfect balance of spices that danced on my palate. Each bite of robust meat is complemented by a subtle kick, making it a true fiesta in a bowl. The inviting atmosphere and friendly staff made for a warm dining experience, enhancing the chili's comforting nature. If you're on a mission to discover Portland’s best chili, Roake’s is a must-visit. You’ll leave with a full belly and a smile! 🌶️

You might also want to check out the best cafe in Portland.