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Music in Pilsen, West Town & the West Side Columbus Day Weekend 2026

Oct 9–12 · 7 picks hand‑checked by Stumblday against organizer pages · updated Oct 6

The 7 best music picks in Pilsen, West Town & the West Side over Columbus Day Weekend (Oct 9–12)

  1. Olivia Rodrigo – The Unraveled Tour — Sun, Oct 11 7:00pm · Pilsen
  2. Olivia Rodrigo: The Unraveled Tour – Night Two — Monday, October 12, 7:00 PM · Pilsen
  3. Armand Hammer with Quelle Chris and Open Mike Eagle — Saturday, October 10; doors 7:00 PM · Pilsen
  4. Afrojack Presents: Control — Friday, October 9 Doors 10 PM · Pilsen
  5. Maddix — Saturday, October 10 Doors 10 PM · Pilsen
  6. Rock and Roll Playhouse – The Music of Grateful Dead for Kids — Sat, Oct 10 11:30am · Pilsen
  7. Emei - Night at the Opera Tour — Sun, Oct 11 7:30pm · Pilsen

About this list

Stumblday's hand-checked ranking of the best music in Pilsen, West Town & the West Side over Columbus Day weekend 2026 (Oct 10–12): 7 picks.

More this weekend across Chicago

Chicago Blackhawks vs. Carolina HurricanesUnited Center, Pilsen, West Town & the West Side
Bank of America Chicago MarathonGrant Park, Downtown, the Loop & West Loop
74th Annual Chicago Columbus Day ParadeDearborn Street, Wacker Drive to Van Buren Street, The Loop
Jerry Seinfeld Live!The Chicago Theatre, Downtown, the Loop & West Loop
Fall Fest at Lincoln Park ZooLincoln Park Zoo, Lincoln Park, Lakeview & Wrigleyville
Abbott Health & Fitness ExpoMcCormick Place, North Building, Hall B1, Near South Side, Downtown, the Loop & West Loop