Explore the Ultimate 2026 Chicago Festival Lineup: Top Food and Music Events in the City and Suburbs

CHICAGO — Planning your summer activities in Chicago? Here’s a selection of both free and ticketed events happening around the city that you won’t want to miss.

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June

The Chicago Blues Festival is set to take place at the Ramova Theatre and Millennium Park from Thursday, June 4, through Sunday, June 7. It’s a must-see for music lovers.

If you’re up for a short trip, Summerfest in Milwaukee kicks off on June 16 and runs through July 4. This renowned festival spans three weekends and promises a diverse lineup of entertainment.

Starting June 15, the Millennium Park Summer Music Series will bring live performances to the Jay Pritzker Pavilion. Enjoy nine concerts scheduled mostly on Mondays and Thursdays.

Art enthusiasts will appreciate the Old Town Art Fair, happening on June 13 and 14 at the Old Town Triangle Center, located at 1763 N. North Park Avenue. It’s a perfect outing for the family.

Finally, for movie buffs, the Millennium Park Summer Film Series begins on June 30. Catch a film every Tuesday through August 18 at the Jay Pritzker Pavilion.

July

–Taste of Chicago at Grant Park will be held on Wednesday, July 8 through Sunday, July 12.

–Windy City Smokeout returns for the 13th year outside the United Center from July 8-12. Click here to see the full lineup.

–Chicago Gospel Music Festival at Jay Pritzker Pavilion will be on Friday, July 24 and Saturday, July 25.

–Lollapalooza returns to Grant Park from July 30 through August 2. Click here to see the full lineup.

August

–Ravinia Music Festival returns August 1 through Sept. 19. Click here to see the full lineup.

–Chicago Air and Water Show at North Avenue Beach will be held the weekend of August 15.

–Chicago House Music Festival and Conference at the Cultural Center and Millennium Park will be held Thursday, August 27 through Sunday the 30th.

September

–Chicago Jazz Festival will be held Thursday September 3 through Sunday the 6.

– Organizers announced El Grito Chicago will be back in Grant Park on the weekend of Sept. 12.

Organizers announced El Grito will be back in Grant Park on the weekend of Sept. 12.

-Riot Fest will take place on the weekend of Sept. 18 in Douglass Park.

To learn more about events organized by Chicago’s Department of Cultural Affairs and Special Events, click here.