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Things to do in Chicago on Friday, Oct 16

Fri, Oct 16 · 64 picks hand‑checked by Stumblday against organizer pages · 1 free in the top 10 · updated Sep 29

The 10 best things to do in Chicago on Friday, Oct 16

  1. NBA Preseason: Chicago Bulls vs. Minnesota Timberwolves — Friday, October 16, 7:00 PM–8:30 PM · Pilsen
  2. PFL – Professional Fighters League: Liz Carmouche vs. Jena Bishop — Friday, October 16, 6:00 PM–11:00 PM · Wintrust Arena
  3. La Gradiva — Friday 8pm · Downtown
  4. Live Reading: “Cold Was the Ground” — Friday, October 16, 6:00 PM–8:00 PM · $6 – $8 · Downtown
  5. King's X — Friday, October 16, 7:00 PM · Downtown
  6. Antiporno — Friday 7pm · Lincoln Park
  7. El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival — Friday Oct 16–Oct 17, 2026 · St. Agustine’s College
  8. Grammy elected guitarist Michael Charles at Free Blues Friday — Friday, October 16, 8:00 PM–10:00 PM · Free · Epiphany Center for the Arts
  9. Bob Schneider Live In Concert — Friday, October 16, 7:30 PM–10:30 PM · City Winery
  10. Brad Williams: The Tall Tales Tour — Friday, October 16, 7:30 PM–9:30 PM · Downtown

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About this list

Stumblday's ranked list of the best things to do in Chicago on Friday, October 16: 22 events, led by NBA Preseason: Chicago Bulls vs. Minnesota Timberwolves, PFL – Professional Fighters League: Liz Carmouche vs. Jena Bishop and La Gradiva — each one checked against the organizer's own page. Below them, 42 exhibitions and shows running through the day.