10 Things to Do in Chicago This Week · September 24–27, 2026

Music & Nightlife

DC Ervin

Stand-up comedian DC Ervin takes the stage at Chicago Improv for a Thursday night show.

Thursday, September 24, 2026 7:00 PM · Chicago Improv, Chicago

Virtual Riot x Blanke: Far From Home Tour

Electronic bass music heavyweights Virtual Riot and Blanke bring their Far From Home Tour to Concord Music Hall for a 18+ late-night show.

Friday, September 25, 2026 Doors @ 10:00 PM · Concord Music Hall, Chicago

Jazmyn W at City Winery Chicago

R&B artist Jazmyn W performs a live show at City Winery Chicago in an intimate winery setting.

Thursday, October 1, 2026 7:30 PM · City Winery Chicago

Festivals & Special Events

12th Annual Irish American Movie Hooley Film Festival

The only Irish American film festival in the world returns to the Wilmette Theatre for three days of cinema celebrating Irish American culture.

Friday, September 25, 2026 8:00 PM · Wilmette Theatre, 1122 Central Ave, Wilmette

Free Events

Stories and Music of Resilience

Crossing Borders Music performs a free 50-minute string quartet concert featuring compositions by composers from Uganda, Argentina, the Soviet Union, the Chickasaw Nation, Taiwan, and the US at the Chicago Children's Museum.

Friday, September 25, 2026 11:00 AM · Chicago Children's Museum, 700 E Grand Ave, Chicago

Radical Optimism: Celebrating 100 Years of Oscar Brown Jr. Opening Exhibit

An opening exhibit celebrating the centennial of legendary Chicago jazz musician and activist Oscar Brown Jr.

Sunday, September 27, 2026 · Chicago

Volunteer: Marathon Encouragement Postcard Writing

Join Read & Run Chicago to write encouraging postcards for community members racing the Chicago Marathon 26.2.

Tuesday, September 29, 2026 7:30 PM · Chicago

Outdoors & Active

Running Tour of Freed to Kill with Gera-Lind Kolarik

Read & Run Chicago's September signature event combines a running tour of true-crime Chicago history with author Gera-Lind Kolarik.

Sunday, September 27, 2026 10:00 AM · Chicago

Arts & Culture

Topdog / Underdog

Suzan-Lori Parks' Pulitzer Prize-winning play runs at Steppenwolf Theatre through November 1, 2026.

Friday, September 25, 2026 7:30 PM · Steppenwolf Theatre, 1650 N Halsted St, Chicago

Jaume Plensa: Beyond Silence

International sculptor Jaume Plensa presents new works at Gray Gallery's Chicago location, on view September 17 through December 19.

Saturday, September 26, 2026 · Gray Gallery, 2044 W. Carroll Avenue, Chicago