What to Do in Chicago This Weekend: Events and Festivals

By the Editorial Team · Friday, July 24, 2026

Chicago will host a variety of cultural and entertainment events this weekend, including the WNBA All-Star Game festivities, concerts by artists like Benson Boone and Buddy Guy, and community festivals such as Wicker Park Fest and the Chinatown Summer Fair. These events highlight the city’s vibrant arts scene and offer diverse activities ranging from sports and music to historical celebrations, attracting locals and visitors alike.

Chicago offers a diverse lineup of cultural and entertainment events throughout the weekend, with options spanning sports, music, festivals, and historical celebrations.

On July 24-25, TOGETHXR, an organization focused on promoting women’s sports, will host a series of activities around the city in conjunction with the WNBA All-Star Game scheduled for July 25 at the United Center. Events include a morning run, panel discussions, appearances by athletes such as Diana Taurasi, Chiney Ogwumike, and Jordan Chiles, as well as interactive experiences like an indoor half-court and photo booths. A live taping of the “Everyone Watches Women’s Sports” podcast will also take place at the Chicago Theatre on July 24. The All-Star Game tip-off is set for 7:30 p.m. at the United Center, located at 1901 W. Madison St., with tickets available online.

Music enthusiasts can attend several concerts over the weekend. Benson Boone will perform on July 24 and 25 at the Allstate Arena in Rosemont, presenting songs from his latest single “The Time of My Life” alongside elements of magic and acrobatics. On July 26, R&B artist Daniel Caesar will appear at the United Center with special guest Faye Webster, promoting his recent album “Son of Spergy.” Tickets for these performances range from approximately $40 to nearly $200.

Blues legend Buddy Guy, who recently marked his 90th birthday, will perform a more intimate concert on July 25 at the Chicago Theatre, accompanied by his daughter Carlise Guy and The Nu Blu Band. Meanwhile, the Gospel Music Festival will energize Millennium Park’s Jay Pritzker Pavilion on July 24 and 25, featuring headliners including Tasha Cobbs Leonard, Hezekiah Walker and Love Fellowship Choir, and Ricky Dillard and New G. The free festival runs from midday into the evening, with some performances broadcast on Inspiration 1390.

Other notable music events include Jack White’s show at The Salt Shed Fairgrounds on July 24 and a unique collaboration between St. Vincent and the Chicago Symphony Orchestra at Ravinia Festival on July 25. The latter concert will showcase reimagined tracks from St. Vincent’s catalog, with support from jazz and South Asian fusion artist Arooj Aftab.

Art and community festivals add to the weekend’s offerings. The Wicker Park Fest, running July 24-26 along Milwaukee Avenue, features multiple music stages alongside fashion shows, art installations, wrestling exhibitions, and activities for children and pets. The 46th Chinatown Summer Fair will take place July 25-26 near 2200 S. Wentworth Ave., highlighting traditional lion dances, K-pop competitions, folk arts, martial arts demonstrations, crafts, and food.

Finally, Pullman Railroad Days at Pullman National Historical Park on July 25-26 commemorates the 100th anniversary of electrified rail service in Chicago. Visitors can explore historic Pullman-built train cars, participate in STEAM education activities, enjoy miniature train rides, and attend transit-related exhibits. On July 26, PBS host Geoffrey Baer will discuss his special “Riding the Rails” with former Federal Railroad Administrator Joseph C. Szabo. Admission is $25 for adults and free for children ages 12 and under with a ticket.

Additional information and tickets for these events are available through respective websites.

This article was reported by synthesizing coverage from multiple independent news outlets to present a balanced, unbiased account. Read about our editorial standards. Spotted an error? Let us know.