Chicago’s Busy Aug. 13 to 19 Arts Calendar Packs Sondheim, Buddy Holly and the Return of Fan Expo Into One Crowded Week of Theater, Music and Festivals
CHICAGO, IL — Chicago’s late-summer calendar is stacked with theater openings, concert bills, museum exhibits and neighborhood festivals stretching from the lakefront to the suburbs. The week of Aug. 13 to 19 also brings back fan favorites like Fan Expo Chicago, the Air and Water Show and the World’s Largest Karaoke Party.
From Broadway titles to free outdoor music and art fairs, the lineup gives residents plenty of ways to fill a weeknight or a full weekend. Some events are ticketed and intimate; others are built for crowds, families and anyone looking for one more summer outing.
Theater leads with Sondheim, a robot sibling drama and a Buddy Holly tribute
Among the biggest stage offerings is Kokandy Productions’ “Sunday in the Park with George” at Chopin Theatre, where Stephen Sondheim and James Lapine’s musical follows painter Georges Seurat while reflecting on love, art and the cost of making both.
Writers Theatre opens “Sisters”, Matthew Libby’s drama about Matilda and her AI sister Greta, while Music Theater Works takes on “West Side Story” in Skokie. Later in the month, Drury Lane Theatre will present “Buddy – The Buddy Holly Story,” tracing the rock pioneer’s short life and rise to fame.
Other productions add even more range, including “I Love You Because” at Oil Lamp Theater, “Adolescent Salvation” at Theater Wit, “Hail Mary/Maria” at the same venue and Dionna Griffin-Irons’ solo show “This Is My Moment” at Steppenwolf’s 1700 Theater.
Music ranges from Ravinia storytelling to free neighborhood stages
The music options stretch from polished outdoor performances to open invitation community events. Gregory Alan Isakov brings his reflective songwriting to Ravinia with the Chicago Philharmonic, while Red Wanting Blue plays Robert’s Westside after years of road-worn indie rock and a 13th studio album.
For something looser, the Salt Shed and the Empty Bottle are reviving the World’s Largest Karaoke Party, with singers selected at random on site. Metro’s Hometown Celebration will benefit the Lin Brehmer Scholars Fund, and Black Ensemble Theater’s free Fridays on the Green series continues with soul, jazz and ensemble performances.
Even the museums and civic spaces get in on the act: the Newberry Library is showing “Conceived in Liberty”, a free exhibit of wartime cartoons, caricatures and illustrations from 1812 through 1918 that examines how artists used images to support or question American ideals.
Family crowds, fandom and festival season take over the city
Several of the week’s biggest draws are built for all-ages crowds. The Chicago Air and Water Show returns to the lakefront with the Thunderbirds, Golden Knights and civilian stunt teams, while Fan Expo Chicago lands in Rosemont with a celebrity roster that includes Kurt Russell, Mr. T and multiple Lord of the RingsGooniesStar Trek and Halloween names.
Festival season is running full tilt, too, with Glenwood Avenue Arts Fest, Printer’s Row Art Fest and Little Italy Festa each offering live music, art, food and family activities. Farther south, the Illinois State Fair is underway in Springfield with grandstand concerts, rodeo events, carnival rides and classic fair food.
For Chicago-area readers, the common thread is simple: there is no shortage of ways to plan a night out, a free afternoon or a full weekend before summer slips away.
Chicago's music scene, one story at a time — Chicago Music Guide.
