Go back in time and enjoy oldies and throwback fashion at the 28th annual Retro on Roscoe festival on September 5-7, 2025, in the Roscoe Village neighborhood. Groove to music on three stages, including a family stage, within a six-block stretch of Roscoe Village. Enjoy music from … [Read more...] about Retro on Roscoe Festival
live music
Jeff Fest Arts and Music Festival
The Jefferson Park neighborhood on Chicago's Northwest side will come alive with music and creative arts during the 24th annual Jeff Fest, on August 1-2, 2025. The sprawling seven acres of Jefferson Memorial Park will host this beloved community event, which features tribute bands, … [Read more...] about Jeff Fest Arts and Music Festival
Free Chicago Jazz Festival
Since 1974, jazz fans from all over the globe have flocked to Chicago for the annual Chicago Jazz Festival, which showcases jazz legends as well as up-and-coming musicians. This year's four-day festival will run from August 28 -31, 2025. Celebrate jazz in all its forms in Millennium Park and … [Read more...] about Free Chicago Jazz Festival
Northalsted Market Days
The largest street festival in the Midwest returns to the bustling Lakeview neighborhood for a two-day celebration of music, pride and community. Northalsted Market Days is scheduled for August 8-10, 2025. The 43rd annual festival kicks off with over 250 vendors, five stages and all-day … [Read more...] about Northalsted Market Days
Chicago House Music Festival and Conference
As the birthplace of house music, Chicago always celebrates and honors this influential art form. The Chicago House Music Festival and Conference will bring the music, history and culture of house music into focus on August 21-24, 2025. The four days of free events will feature … [Read more...] about Chicago House Music Festival and Conference
Jazz ‘N on The Steps
Take in the smooth rhythms of jazz during Summer evenings at the Jazz' N on The Steps free event on July 27, 2025, at St. Moses the Black Parish. Hosted by the Southside Jazz Coalition, this popular community concert features well-known jazz vocalists and musicians performing on the … [Read more...] about Jazz ‘N on The Steps
Wrigleyville Night Market
Summer nights just got more exciting with the start of the weekly Wrigleyville Night Markets at Gallagher Way, kicking off on July 10, 2025, through September 18, 2025. Enjoy strolling through over 50 vendors displaying vintage clothing, jewelry, home goods and lots of unexpected finds. … [Read more...] about Wrigleyville Night Market
Passport Vibes: Afrobeat Street Festival
Dance to the joyful, contagious rhythms of Afrobeat music during the free Afrobeat Street Festival on July 13, 2025, in the Hyde Park neighborhood. Explore the culture of Afrobeat, a genre created in Nigeria by the legendary musician Fela Kuti, with DJs from around the world … [Read more...] about Passport Vibes: Afrobeat Street Festival
Barrio Arts Festival
The signature festival of the National Museum of Puerto Rican Arts & Culture, the Barrio Arts Fest, returns to Humboldt Park on July 12-13,2025. Immerse yourself in the richness of Puerto Rican culture during this highly anticipated free festival on the grounds of the … [Read more...] about Barrio Arts Festival
Andersonville Vintage Market
The Chicago shopping event of the summer returns; the fifth annual Andersonville Vintage Market will supply treasures from every era on select Sundays on July 20, August 17. September 21 and October 19, 2025. Discover one-of-a-kind antiques, jewelry, furniture, art, clothing and more at … [Read more...] about Andersonville Vintage Market
Ravenswood on Tap
Head to Malt Row, Ravenswood's bustling craft beer community to sip your way through the annual Ravenswood on Tap festival on July 19 - 20, 2025. The festival showcases the neighborhood's small craft breweries, including Koval, Dovetail, Half Acre and more. Enjoy fresh brews and cocktails as … [Read more...] about Ravenswood on Tap
Live on the Lake Free Summer Concerts
Music fans can enjoy the beauty of lakeside views as well as live melodies during the free weekly Live on the Lake summer concert series at the Navy Pier Beer Garden. every weekend, through September 1, 2025. Grab a cold one from Tangled Roots Brewery or nibble on nachos or a brat, while … [Read more...] about Live on the Lake Free Summer Concerts
