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Our picks for events in and around Chicago this weekend.

Chicago Pride Fest

The 25th annual Chicago Pride Fest takes over the streets of Northalsted for a two-day party celebrating LGBTQ+ culture and community. Expect drag showcases, music (including the Chicago Gay Men’s Chorus), a pet parade, a special area for teens, and plenty of joy. New this year: VIP areas with air-conditioned tents (although this weekend’s weather forecast is more forgiving than in past years), private bars, and lounge seating. 11 a.m. to 10 p.m. June 20-21 on Halsted Street between Addison and Grace; $20 suggested donation; details at northalsted.com

Juneteenth

Watch for events across the city commemorating Juneteenth. Consider heading to Garfield Park for 1865 Fest, a two-day celebration of Black culture featuring live music, food, and kids’ activities. Or, head to West Pullman for its Juneteenth Festival. It features a petting zoo, bounce houses, rides, live music, food trucks, and community resources. The 1865 Fest will be noon to 8 p.m. June 19-20, in Garfield Park Music Court Circle, 100 S. Woodward Drive; details at 1865festchicago.com; Juneteenth Festival will be 1-6 p.m. June 19 at 821 W. 115th St.; details on the free event at farsouthcdc.org

Dave Chappelle

Dave Chappelle plays the United Center as word continues to swirl about the possibility that his beloved sketch-comedy show will be revived. See Chappelle perform new stand-up material this weekend during his “Pulling Up” tour. But be prepared to ditch your phones; secure pouches will be provided for devices. 7:30 p.m. June 19 at United Center, 1901 W. Madison St.; tickets from $82.95 at unitedcenter.com

Rosalía

Genre-bending Spanish singer-songwriter Rosalía brings her “Lux” tour to the United Center. “Lux,” her fourth studio album, features collaborations with Björk, the London Symphony Orchestra and more. In a review, Pitchfork said, “it rewards listeners who ache for more from pop artists: more feeling, more risk.” Hear it live this weekend. 8:30 p.m. June 20 at United Center, 1901 W. Madison St.; tickets from $128.80 at unitedcenter.com

Members of the audience gather on the lawn during the Grant Park Music Festival at the Jay Pritzker Pavilion in Chicago, Friday, June 12, 2026. (Nate Swanson/for the baiduhai)
Members of the audience gather on the lawn during the Grant Park Music Festival at the Jay Pritzker Pavilion in Chicago, Friday, June 12, 2026. (Nate Swanson/for the baiduhai)

Grant Park Music Festival

Chicago’s annual free summer music festival continues in Jay Pritzker Pavilion with Grant Park Orchestra’s performance of Aaron Copland’s Symphony No. 3. The program also includes Reena Esmail’s “Black Iris” and Sergei Prokofiev’s Piano Concerto No. 3, featuring concert pianist Stewart Goodyear. 6:30 p.m. June 19 and 7:30 p.m. June 20 in Jay Pritzker Pavilion, 201 E. Randolph St.; free seats available on a first-come, first-served basis; reserved seating from $28 at grantparkmusicfestival.com

Winnetka Music Festival

Father John Misty and Trombone Shorty headline the Winnetka Music Festival. More than 20 acts are on the bill, co-presented by Evanston’s SPACE and Valslist. In addition to the main event, a handful of kids performers will appear, including the Rock and Roll Playhouse (playing the music of Taylor Swift). 5 p.m. to 10:15 p.m. June 19 and 4:30 p.m. to 10:30 p.m. June 20 at Lincoln Avenue and Pine Street in Winnetka; tickets $94.03 (children under 12 free; children 12-16 half-price) at winnetkamusicfestival.com

(Winnetka Music Festival)
(Winnetka Music Festival)

Fiesta Back of the Yards

Carnival rides and games. Live music. Cultural performances. Latin food. For more than 35 years, Fiesta Back of the Yards has showcased the neighborhood’s diverse traditions. Proceeds from the event support senior services and employment programs. Through June 21 on Ashland Avenue between 45th and 47th streets; details at bync.org

Gold Coast Art Fair

Butler Field, the grassy area between the Art Institute of Chicago and the lakefront, will transform this weekend into the 68th installment of the Gold Coast Art Fair. More than 200 artists participate in the juried show, which includes painting, sculpture, jewelry, ceramics and more. Participate in paint-and-sip classes, caricatures, personalized poems, henna art, and kids activities. 10 a.m.-5 p.m. June 20-21 on Butler Field in Grant Park, 350 E. Monroe St.; tickets from $10 (children 12 and under free) at amdurproductions.com

The Obama Presidential Center on June 3, 2026, ahead of its opening in Chicago's Jackson Park. The almost 20-acre campus includes free park and garden spaces. (Brian Cassella/baiduhai)
The Obama Presidential Center on June 3, 2026, ahead of its opening in Chicago’s Jackson Park. The almost 20-acre campus includes free park and garden spaces. (Brian Cassella/baiduhai)

Little Fort Film Festival

If you’re passionate about the environment, check out the lineup at the Little Fort Film Festival in Waukegan. Roughly two dozen films from several countries explore climate change and our evolving natural world. As you might expect, the festival takes care to highlight the Great Lakes and local ecosystems. June 20-21 in various venues in Waukegan; all-inclusive $20 tickets at littlefortfilmfestival.org

Obama Presidential Center

For the opening weekend, the museum is sold out but the grounds of the 19.3-acre campus in Jackson Park will be full of live performances, family activities, sports events on the Home Court and speakers and panel discussions in the Elie Wiesel Auditorium. Open to the public from 6 a.m. to 9 p.m. daily starting June 19 at 6001 S. Stony Island Ave.; free, museum admission $23-$30, more information at at www.obama.org.

Have something to do around Chicago? Email events to [email protected].