Crashing Out Live – Chicago, IL – 2026 Tour

Philip DeFranco & Alex Pearlman are taking the meltdown on the road. Since society is crumbling we might as well laugh at it together. Crashing Out Live is the live tour extension of Crashing Out with Philip DeFranco and Alex Pearlman, a popular news and comedy podcast. The show features internet personality and news commentator Philip DeFranco alongside co-host Alex Pearlman, where they process c

More on Saturday →

Hyde Park Jazz Festival 2026Saturday and Sunday, September 26–27, 2026; set times vary by venueMultiple Hyde Park venues, Hyde Park, Bronzeville & the South SideFreeOne Weekend Only

Foster The People – Good Mourning Sunshine TourSat, Sep 26, 2026 · 8:00pmHuntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopOne Day Only

WWE: Worlds Collide – Rosemont, ILSaturday, September 26, 2026, 7:30 PM (doors 90 minutes before)Allstate Arena, 6920 North Mannheim Road, Evanston & Oak ParkOne Day Only

Beatdown Sound System's Vibrations of Freedom at World Music Festival ChicagoSaturday, September 26, 2026, 1–7 p.m.Ping Tom Memorial Park, Chinatown, Downtown, the Loop & West LoopFREEOne Day Only

Also in Lincoln Park, Lakeview & Wrigleyville

Cold Waves XIV: Stabbing Westward, TR/ST, King Woman and More (18 and Over)Friday–Sunday, September 25–27, 2026; doors 6 p.m., show 7 p.m. each nightMetro, 3730 N. Clark St., Lincoln Park, Lakeview & Wrigleyville$55 advanceOne Weekend Only

Oktoberfest Chicago at St. AlphonsusSeptember 25–27, 2026; Friday 5–10 p.m., Saturday noon–10 p.m., Sunday noon–7 p.m.St. Alphonsus Church grounds, Lakeview, Lincoln Park, Lakeview & Wrigleyville$10 Friday and SaturdayOne Weekend Only

Reeling 2026: The 44th Chicago LGBTQ+ International Film FestivalSeptember 17–27, 2026; screening times varyLandmark Century Centre Cinema, Lakeview, Lincoln Park, Lakeview & Wrigleyville$15 general admission ($13 me…Limited Run

More comedy this weekend →

Martin Lawrence – Y’all Still Know What It Is! TourFri, Sep 25, 2026 · 8:00pmArie Crown Theater, Downtown, the Loop & West LoopOne Day Only

Bassem Youssef – The Belly of the Beast TourSat, Sep 26, 2026 · 7:00pmThe Chicago Theatre, The Loop, Downtown, the Loop & West LoopOne Day Only

See the full ranked weekend board →