Fall Entertainment Season Hits Full Swing: Film Fest, Prine Tribute Week, Open House Chicago on Deck

CHICAGO URBAN DAILY

CHICAGO (CHICAGO URBAN DAILY)— Fall is officially Chicago’s season, and the calendar proves it. The city’s biggest October events are stacking up back to back, giving Chicagoans more reasons than ever to get out and take the city in.

The Chicago International Film Festival returns October 14–25 with its 2026 edition — feature films, documentaries, and shorts from around the world. It remains one of the signature fall arts events in the city.

Before that, the city honors one of its own. October 7–11 brings a string of events marking what would have been John Prine’s 80th birthday. The centerpiece is an October 8 concert at the Chicago Theatre featuring Alejandro Escovedo, Steve Earle, Margo Price, Amos Lee, Josh Ritter, Hayes Carll and The Cactus Blossoms. The tribute also includes “John Prine’s Chicago” at the Chicago History Museum on October 9, a daylong celebration at the Old Town School of Folk Music on October 10, and a trolley tour of Maywood — Prine’s hometown — on October 11.

And mark October 17–18 for Open House Chicago, which opens the doors to more than 200 architecturally and historically significant spaces across 25-plus neighborhoods, with free admission.

Today is also the closing day of the citywide World Music Festival Chicago, which ran September 25 through October 4.

Stay tuned to Chicago Urban Daily for more on the fall season across Chicagoland.

Reported by Chicago Urban Daily News. Visit chicagourbandailynews.com for updates.

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