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Music in Chicago on Columbus Day Monday, Oct 12

Columbus Day Monday, Oct 12 · 6 picks hand‑checked by Stumblday against organizer pages · 1 free in the top 6 · updated Oct 6

The 6 best music picks in Chicago on Columbus Day Monday, Oct 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. Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour — Sep 18–Oct 17, 2026 · Downtown
  4. Indigenous Peoples' Day featuring Colectivo Sayba, Tamanaco Tambor & Trio Axol — Monday, October 12, 7:30pm · Free · Lincoln Square
  5. Inoha — Mon, Oct 12 6:30pm · Lincoln Park
  6. Chicago By Night River & Lake — Sep 18–Oct 18, 2026 · $50 · Chicago’s First Lady Cruises

About this list

Stumblday's hand-checked ranking of the best music in Chicago on Columbus Day Monday, Oct 12: 6 picks, refreshed weekly.

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