Things to Do in Chicago on Saturday, Columbus Day Weekend 2026

Saturday, Oct 10 · 190 picks hand‑checked by Stumblday against organizer pages · 2 free in the top 10 · updated Oct 6

The 10 best things to do in Chicago on Saturday, Oct 10

  1. Chicago Blackhawks vs. Carolina Hurricanes — Sat, Oct 10 6:00pm · Pilsen
  2. Jerry Seinfeld Live! — Fri, Oct 9 7pm; Sat, Oct 10 · 5pm and 8pm · Downtown
  3. Fall Fest at Lincoln Park Zoo — Sep 25–Oct 18, 2026 · Free · Lincoln Park
  4. Abbott Health & Fitness Expo — Thursday, October 8 – Saturday, October 10 · Free · Downtown
  5. Beck – Ride Lonesome Tour — Fri, Oct 9 8:00pm · Downtown
  6. Chicago Fire FC vs. New York City FC — Saturday, October 10, 1:30 PM · Downtown
  7. Lincoln Park Wine Fest — October 9–11; Friday 5–10pm · General admission from $30 · Lincoln Park
  8. Chicago Art Fair — October 7–10 Wed 5–8 PM; Thu–Fri 11 AM–8 PM · Downtown
  9. Operation Mincemeat: A New Musical — Through Oct 11 · Downtown
  10. Don Giovanni — Oct 10–Oct 18, 2026 · Lyric Opera House

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About this list

Stumblday's hand-checked ranking of the best things to do in Chicago on Saturday of Columbus Day weekend, Oct 10: 190 picks, refreshed weekly.

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