Jennifer Day

Jennifer Day is a freelance writer for the Chicago Tribune.

Ariana Grande performs during the last day of the 2019 Lollapalooza Music Festival in Grant Park on Aug. 4, 2019, in Chicago. (Armando L. Sanchez/Chicago Tribune)

What to do in Chicago: Ariana Grande, the Sports Collectors Convention and, of course, Lollapalooza

July 30, 2026 at 5:00 a.m.

Around the area in the days ahead, Lollapalooza in Grant Park, both Ariana Grande and monster trucks at the United Center, and a joint concert by Chicago and Styx.

Benson Boone performs on the IHG Hotels & Resorts stage during Lollapalooza at Grant Park on Aug. 1, 2024. (Eileen T. Meslar/Chicago Tribune)

What to do in Chicago: The WNBA All-Star Game, Benson Boone and Buddy Guy at 90

July 23, 2026 at 5:30 a.m.

This weekend's events in Chicago also include Gospel Music Festival, Wicker Park Fest and the Chinatown Summer Fair.

Paul Simon performs at Symphony Center in Chicago on May 21, 2025. (Chris Sweda/Chicago Tribune)

What to do in Chicago: Sharks at Shedd and concerts by Paul Simon, Melanie Martinez and Rush

July 16, 2026 at 11:25 a.m.

On a big weekend for live music, there's also a car show at SeatGeek Stadium, the Southside Summer Festival and a return for the Silver Room Sound System Block Party.

People watch as Parker McCollum performs at the annual Windy City Smokeout outside of the United Center in Chicago on Friday, July 12, 2024. (Chris Sweda/Chicago Tribune)

What to do in Chicago: Taste of Chicago, Windy City Smokeout and all things Godzilla in Rosemont

July 10, 2026 at 10:29 a.m.

Around the area this weekend, Taste of Chicago has food, music and another chance for fireworks, G-Fest stomps into the western 'burbs and Lizzo headlines a concert to inaugurate the...

People celebrate Independence Day by watching fireworks at Chicago’s Navy Pier on July 3, 2024. (Chris Sweda/Chicago Tribune)

What to do in Chicago: Fourth of July parades and the Tinley Park Country Fest

July 2, 2026 at 5:00 a.m.

Around the area this weekend, plenty of parades and fireworks for the Fourth of July, plus exhibits at the Chicago History Museum and American Writers Museum.

Participants march with balloons in the annual Chicago Pride Parade on June 29, 2025, in Lakeview. (Brian Cassella/Chicago Tribune)

What to do in Chicago: Pride Parade, ‘Weird Al’ and the Logan Square Arts Festival

June 25, 2026 at 5:00 a.m.

Around the area this weekend, Chicago's annual Pride Parade processes through the streets of Lakeview and “Weird Al” Yankovic, Lionel Richie and Earth, Wind and Fire are all at the...

Dave Chappelle performs during a fundraiser for the Duke Ellington School of the Arts in Washington, D.C., in June 2022. (Gemunu Amarasinghe/AP)

What to do in Chicago: Dave Chappelle, Pride Fest and the big Obama center opening weekend

June 18, 2026 at 5:00 a.m.

Here are our picks for events in and around Chicago this weekend.

Lupe Fiasco performs at Riot Fest in Chicago's Douglass Park on Sept. 17, 2021.

What to do in Chicago: Lupe Fiasco, Red Bull on a bike and a new pinball museum

June 11, 2026 at 5:00 a.m.

Around the area this weekend, The Flip opens as a nonprofit museum and arcade, Nate Bargatze comes to Rosemont, and the Old Town neighborhood is full of art fairs.

Musician Jack Antonoff and the Bleachers perform at Verizon Wireless Music Center on May 31, 2014, in Irvine, California. (Christopher Polk/Getty Images)

What to do in Chicago: The Blues Festival, Bleachers and bubbles at the Botanic Garden

June 4, 2026 at 5:00 a.m.

Along with the Blues Festival in Millennium Park, the American Writers Festival welcomes visitors on Michigan Avenue and Harold Washington Library, and the Midwest Haunters Convention takes over Rosemont.

Jenny Lewis leads Rilo Kiley at Riot Fest in Chicago’s Douglass Park on Sept. 19, 2025. (Chris Sweda/Chicago Tribune)

What to do in Chicago: Rilo Kiley, Summer Walker and running with the dinosaurs

May 28, 2026 at 11:45 a.m.

Around the area this weekend, Do Division Street Fest, the Dino Dash at Brookfield Zoo, and loads of concerts at the start of live music season.

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