10 Chicago Festivals to Keep You Partying Year-round

If you're going to start somewhere, start big. Lollapalooza takes over Grant Park for four days every summer — typically late July or early August — attracting fans from around the globe. The lineup of musical acts spans every genre imaginable, from pop to punk, hip-hop to house music.

Think of it like a musical buffet, except the main course is your favorite band, live and loud.

This one's a soul-stirrer. The Chicago Blues Festival is the largest free blues festival in the world.

Held in Millennium Park every June, it celebrates the city's deep blues heritage with legendary performers and emerging artists alike. It's a toe-tapping tribute to the sounds that helped shape American music.

Swing into Labor Day weekend with the Chicago Jazz Festival, a celebration of jazz that’s been going strong since 1979. Set in venues like the Chicago Cultural Center and Millennium Park, this free festival delivers everything from bebop to big band.

And yes, there’s plenty of room to dance.

Born in Chicago and celebrated worldwide, house music gets its due in this unique event. Held in August, the Chicago House Music Festival features top DJs and special events that dig into the genre’s roots and its global reach.

Expect outdoor concerts, dance floors in the park, and a sound that gets under your skin — in a good way.

This isn’t just a festival. It’s a season-long dance party. Chicago SummerDance brings dance lessons, live music, and open-air joy to parks across the city from June to September. Swing in Grant Park, salsa in Humboldt Park, or try something new in Logan Square.

No partner? No problem.

Food festivals don’t get much more iconic than this. Taste of Chicago in Grant Park, held in September, dishes out everything from classic Chicago hot dogs to global gourmet bites. Vendors come from across the city to serve up flavors that reflect Chicago’s culinary diversity.

Bring your appetite and stretchy pants.

This music and food festival in the Hyde Park neighborhood celebrates Black culture and community. Think big-name artists, local DJs, mouthwatering eats and craft vendors — all wrapped up in a festive weekend in mid-June. It’s like a block party turned up to 11.

Late August and early September in the West Loop means art, crafts and live music galore.

This fest transforms a stretch of Fulton Street into an open-air gallery filled with local artists, food vendors and beer gardens. Whether you're shopping for handmade jewelry or just browsing, it’s a feast for the senses.

Fall gets a sweet and spicy upgrade in this early October event that celebrates the apple in all its glory. Think fresh cider, pie and caramel-covered everything — plus music, crafts and family friendly events. It’s the perfect excuse to get outside and enjoy the season.

Though technically not a music or food fest, this August staple in the skies over Lake Michigan deserves a shoutout. With daredevil pilots and roaring jets, it’s the biggest free-admission air and water show of its kind in the U.S. — a guaranteed crowd-pleaser.

We created this article in conjunction with AI technology, then made sure it was fact-checked and edited by a HowStuffWorks editor.