Milwaukee's Best Chili Guide

Finding exceptional chili across the greater Milwaukee area means discovering everything from a legendary 90-year-old chili parlor downtown to award-winning smoked meat creations in the North Shore suburbs. Milwaukee hosts Wisconsin's largest restaurant chili cook-off and features dedicated chili trails, making this region a surprisingly rich destination for chili enthusiasts. This comprehensive guide organizes the best spots geographically so families can plan efficient outings—whether you're in the mood for a quick weekday lunch or a weekend chili adventure.

North Shore communities

The Ozaukee County Chili Trail, typically held January through February, connects dozens of participating restaurants across Mequon, Cedarburg, and Grafton, making winter an ideal time to explore this area's chili scene. Several standout destinations operate year-round.

Highland House in Mequon (12741 N. Port Washington Rd.) serves what may be the most distinctive chili in the North Shore: Smoked Tri-Tip and Braised Short Rib Chili with shredded cheese, sour cream, and oyster crackers ($5.50+). Beyond the premium chili, families appreciate the video game room for children, one of the Midwest's best outdoor patios (seasonal), and accommodations for large groups up to 20 people. Open daily with a kids' menu available. Phone: (262) 243-5844.

Kurt Schulz Delicatessen and Pastry Shoppe in Brown Deer (8752 N. Deerwood Dr.) has earned rave reviews, with visitors calling their chili "the best I've ever eaten." This family-owned establishment in Historic Brown Deer Village serves chili as part of rotating soup specials—call ahead at (414) 354-1004 to confirm availability. Hours: Tuesday through Saturday, 6:30 AM to 3:00 PM (breakfast and lunch only). Budget-friendly pricing and a private party room make this ideal for family gatherings.

The Bay Restaurant in Whitefish Bay (342 E. Silver Spring Dr.) offers daily Beef Bean Chili—a hearty, chunky style described as "beany, meaty, tomatoey." The 1955 historic building provides a casual dining atmosphere with a dedicated kids' menu. Chili prices run $3 for a cup, $6 for a bowl. Hours: Tuesday through Sunday (closed Mondays), with weekend brunch available. Wheelchair accessible with public parking behind the restaurant.

Harry's Bar & Grill in Shorewood (3549 N. Oakland Ave.) serves seasonal Chicken Chili during colder months—tomato-based and rich with chicken pieces, served with optional cheese, onions, and sour cream. This 28-year neighborhood establishment offers a family-friendly atmosphere with large windows and excellent service. Moderate pricing ($13-17 entrees).

Anvil Pub & Grille in Cedarburg (N70 W6340 Bridge Rd.) occupies a restored 19th-century blacksmith's shop within Cedar Creek Settlement, offering chili in a truly unique setting. The outdoor patio overlooks Cedar Creek Waterfall. Verified as good for kids on Yelp, with moderate pricing ($12-25 entrees). Phone: (262) 376-2163.

Additional Ozaukee County Chili Trail participants worth noting include Crave Bar and Food (10401 N. Port Washington Rd., Mequon), Cedars Bowling Center (W53N404 Park Cir., Cedarburg—great for combining bowling with chili), and Juice's Ghost Town (990 Ulao Rd., Grafton—traditional supper club atmosphere).

Downtown Milwaukee

Real Chili stands as Milwaukee's definitive chili destination and the city's only dedicated chili restaurant—operating continuously since 1931. Only seven people have ever known the secret recipe, and the restaurant uses the same spice vendor and meat distributor it started with over 90 years ago. Featured on Food Network, this is essential eating for any chili lover.

Real Chili operates two locations: Downtown at 419 E. Wells Street (Mon-Wed 11am-10pm; Thu 11am-2:30am; Fri-Sat 11am-3am; closed Sunday) and near Marquette University at 1625 W. Wells Street (Mon-Wed 11am-12am; Thu 11am-2:30am; Fri-Sat 11am-3am; Sun 11am-10pm). Choose your heat level (mild, medium, or hot) and customize with beans, meat, spaghetti, cheese, onions, or sour cream. The "Marquette Special" combines meat, beans, and spaghetti—essentially Cincinnati-style. Prices run $3-$8 per bowl, making this extremely affordable. Families appreciate the counter-service format and simple menu including hot dogs and chili cheese dogs. The downtown location serves alcohol and offers catering.

Swingin' Door Exchange (219 E. Michigan St.) inhabits a historic 1930s saloon in the landmark Mackie/Grain Exchange Building, serving homemade chili with ground beef (no beans) amid stained-glass lamps and vintage charm. Chili runs $3-$5, full meals $4-$29. Open Monday through Sunday with sidewalk seating available.

Smoke Shack in the Third Ward (332 N. Milwaukee St.) offers White Chili as a unique BBQ option. This rustic Southern-style establishment uses certified humanely-raised meats and features an "escape the city" outdoor patio. Kid-friendly BBQ options and gluten-free items available. Moderate-to-upscale pricing ($15-30 entrees). Hours: Sun-Thu 11am-9pm; Fri-Sat 11am-10pm.

Beans & Barley (1901 E. North Ave.) has served Vegetarian Chili daily since 1979—made with red beans, bulgur wheat, tomato, onion, peppers, and secret spices. Prices: Cup $2.75, Bowl $3.50, Quart $7.00. The dedicated kids' menu and health-food market make this perfect for families with dietary restrictions. IMPORTANT: Beans & Barley closes permanently January 31, 2026—visit soon to experience this beloved 53-year Milwaukee institution.

Fuel Cafe operates in both Riverwest (818 E. Center St.) and Walker's Point (630 S. 5th St.), serving different vegan/vegetarian chili recipes every weekend. The legendary 1993 coffee shop features motorcycle-themed décor and outdoor seating. Budget-friendly at $5-8 for sandwiches.

Valley Inn (4000 W. Clybourn St.) is a genuine hidden gem—family-owned since 1959 in the Piggsville neighborhood near Miller Brewery and American Family Field. Homemade chili features regularly alongside famous fish fry and handmade pizzas. Very affordable with free parking.

Milwaukee breweries and sports bars

Lakefront Brewery (1872 N. Commerce St.) serves Vegetarian 4-Bean Chili topped with smoky gouda, oyster crackers, and jalapeño wheels for just $5. The brewery has won "Best Heat" at Rockabilly Chili multiple consecutive years. Explicitly family-friendly ("kids are welcome!"), the European-inspired beer hall offers spacious seating, a famous Friday Fish Fry with live polka music, and a spectacular Milwaukee River patio with skyline views. One of Milwaukee's most popular brewery tours (80,000+ annual visitors). Hours: Mon-Thu 3pm-9pm; Fri-Sat 11am-9pm; Sun 11am-5pm.

Major Goolsby's (340 W. Kilbourn Ave.) ranks #4 Best Sports Bar in America according to Sports Illustrated. Since 1970, this Milwaukee institution has served "Jerry's kick-ass army recipe" chili and famous Chili Dogs ($9.94). With 50+ HDTVs, four massive video walls, and walls covered in autographed sports memorabilia, this is perfect for sports-loving families. The venue explicitly welcomes "patrons of all ages" in a "family-friendly atmosphere." Located across from Fiserv Forum—ideal before or after Bucks games.

Motor Bar & Restaurant at the Harley-Davidson Museum (400 W. Canal St.) offers both Roadhouse Beef Chili (Wisconsin cheddar cheese crisp, sour cream, scallions—$9) and Smokehouse Vegan Chili (pickled red onion, tortilla crisps, cilantro—$9). The location on the Harley-Davidson Museum campus makes this ideal for family outings, with scenic Menomonee River views and what many call "the best patio in Milwaukee." Free parking on the 20-acre museum campus.

Crafty Cow operates three family-friendly locations—Bay View (2671 S. Kinnickinnic Ave.), Wauwatosa, and Oconomowoc. The family-owned establishment earned runner-up for "Best Heat" at 2024 Rockabilly Chili and offers creative chili-infused items. Weekend brunch available.

Suburban spots

Kettle Range Meat Co. in Elm Grove (13402 Watertown Plank Rd.) has won "Best Meat" at Rockabilly Chili five times (2019, 2020, 2021, 2022, 2025). Their award-winning chili is available by the pint for take-home—made with locally-sourced, grass-fed beef from family farms. Perfect for families who want quality chili at home. Hours: Mon-Fri 10am-7pm; Sat-Sun 9am-5pm. Also operates a Milwaukee location at 5501 W. State St.

Camino in West Allis (7211 W. Greenfield Ave.) serves 3 Bean Chorizo Chili ($7) made with house-made chorizo, plus Chili Cheese Fries topped with the same chorizo chili and shredded cheddar. Add fixins (onion, sour cream, cheese, jalapeños) for $1 extra. Named one of West Allis's Essential Restaurants and won runner-up for "Best Meat" at 2022 Rockabilly Chili. $5 burger Mondays offer great family value.

Joe's K Ranch in Cudahy (4840 S. Whitnall Ave.) has served the community since 1958. Their Loaded Chili comes topped with jalapeños, onion, bacon, tots, grated cheese, and sour cream. This classic supper pub offers sand volleyball courts and horseshoe courts for outdoor family fun, plus excellent value pricing. Hours: Mon 11am-11pm; Tue-Sat 11am-12am; Sun 11am-10pm.

Double B's BBQ in West Allis (7412 W. Greenfield Ave.) ranks #4 Best BBQ on Milwaukee A-List. House-made chili rotates as soup of the day—call ahead to confirm availability. Six homemade BBQ sauces with various heat levels. Family-friendly with a spacious modern dining room.

The Saucy Swine in St. Francis (2245 E. Saint Francis Ave.) brings "BBQ with a twist," featuring Cornbread with Green Chilis (baked with corn, sharp cheddar, and mild green chilis) and "Smoke n' Fire" sauce made with habanero, chipotle, and jalapeño. Chef-owned with Friday fish fry available.

Annual events and competitions

WMSE Rockabilly Chili is Wisconsin's largest restaurant chili cook-off, held annually in late March at MSOE Kern Center (1245 N. Broadway, Milwaukee). Now in its 23rd year, over 40 restaurants compete in categories including Best Meat, Best Veggie, Best Heat, Most Unique, and Best Display.

Family-friendly features include chili pepper mascot races (similar to the famous Miller Park sausage races), children's coloring activities on placemats, a dedicated kids' area by Artists Working in Education (AWE), and DJs spinning music throughout. Admission: $12 advance tickets (includes 4 chili samples); additional samples $1 each; children 10 and under enter FREE. Donate 2+ non-perishable items to Hunger Task Force and receive 2 extra samples. Tickets available at wmse.org/chili.

Oconomowoc Chili Fest (17th Annual on January 31, 2026) offers a winter-friendly indoor downtown walking event where up to 25 local businesses prepare specialty chilis, signature dishes, and Bloody Marys. Location: Downtown Oconomowoc (173 E. Wisconsin Ave.). Contact: Oconomowoc Area Chamber of Commerce, (262) 567-2666.

Chilimania in Edgerton (55 miles southwest of Milwaukee) hosts the Wisconsin State CASI Championship the weekend after Labor Day. This 35-year tradition features a Friday night country concert, Saturday CASI competition, and public chili tasting starting at 3 PM. The 501(c)3 nonprofit has raised over $200,000 for youth education scholarships since 1990.

Wisconsin State ICS Chili Cook-Off in Green Lake (85 miles northwest) takes place the first Saturday after Labor Day at Deacon Mills Park. ICS-sanctioned competition in Traditional Red, Homestyle, and Vegetarian categories; public tasting begins at 3 PM.

Menomonee Falls Downtown Harvest Fest (October 4, 2025) at Mill Pond Park features an 8-restaurant chili cook-off with people's choice voting. Free admission with $10 chili tasting fee. Exceptional family programming includes wagon rides through historic downtown, s'mores by the fire, kids' crafts, toddler play area, princess meet-and-greet, and a free evening concert.

The Ozaukee County Chili Trail (January-February) organized by Mel's Charities connects participating restaurants across the North Shore for competitive "Best Chili" honors while raising money for charity.

Specialty styles and dietary options abound across the region

Cincinnati-style chili (served over spaghetti): Real Chili's "Marquette Special" is the definitive local example.

White chili: Smoke Shack (Third Ward) and Harry's Bar & Grill (Shorewood, seasonal).

Chorizo chili: Camino (West Allis) features house-made chorizo in their 3 Bean Chorizo Chili.

Smoked meat chili: Highland House (Mequon) with Smoked Tri-Tip and Braised Short Rib, and Kettle Range Meat Co. (Elm Grove) for their competition-winning recipes.

Vegetarian options: Beans & Barley (through January 2026), Fuel Cafe (weekends), Lakefront Brewery (4-bean chili with smoky gouda), and Real Chili (soy-free, dairy-free, gluten-free vegetarian chili).

Vegan options: Fuel Cafe (different recipe each weekend), Motor Bar at Harley-Davidson (Smokehouse Vegan Chili).

Planning your family chili adventure

For a North Shore day trip, combine Highland House's video game room and premium chili with a stroll through historic downtown Cedarburg and Anvil Pub & Grille's waterfall patio views. In winter, follow the Ozaukee County Chili Trail to sample multiple locations.

For downtown Milwaukee, Real Chili is non-negotiable for any first-time visitor. Add the Harley-Davidson Museum with chili at Motor Bar, or catch a Bucks game with pre-game chili at Major Goolsby's. Lakefront Brewery combines award-winning vegetarian chili with a family-friendly brewery tour.

For suburban exploration, Kettle Range Meat Co. in Elm Grove offers take-home pints of competition-winning chili, while Joe's K Ranch in Cudahy provides classic Wisconsin supper club atmosphere with loaded chili and outdoor games.

Best budget options: Real Chili ($3-$8), Beans & Barley ($2.75-$7), Lakefront Brewery ($5), and Valley Inn.

Best for picky eaters: Real Chili (simple customization), Crafty Cow (familiar comfort food), and any Chili's Grill & Bar location for consistent chain quality.

Conclusion

Milwaukee's chili scene rewards adventurous families with far more variety than most expect from a city better known for beer and cheese curds. The convergence of a 90-year-old chili institution, award-winning competition cooks at local butcher shops, and Wisconsin's largest restaurant chili cook-off creates genuine depth for exploration. Seasonal events like the Ozaukee County Chili Trail and Rockabilly Chili transform winter and early spring into peak chili season, while year-round destinations from Mequon's Highland House to downtown's Real Chili ensure a satisfying bowl awaits regardless of timing. For North Shore families specifically, the concentration of quality options from Brown Deer through Cedarburg makes chili a legitimate culinary adventure—one that pairs naturally with the region's historic downtowns, family-friendly breweries, and welcoming supper clubs.