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Date night in Chicago on Friday, Oct 16

Fri, Oct 16 · 32 picks hand‑checked by Stumblday against organizer pages · updated Sep 29

The 10 best date night in Chicago on Friday, Oct 16

  1. La Gradiva — Friday 8pm · Downtown
  2. Live Reading: “Cold Was the Ground” — Friday, October 16, 6:00 PM–8:00 PM · $6 – $8 · Downtown
  3. Antiporno — Friday 7pm · Lincoln Park
  4. El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival — Friday Oct 16–Oct 17, 2026 · St. Agustine’s College
  5. Nowhere to Lay My Eyes — Friday 3pm · Downtown
  6. OFF Book: The Improvised Musical Podcast — Friday, October 16, 7:30 PM–9:30 PM · Lincoln Park
  7. Takes All Kinds — Friday, October 16, 7:30 PM–9:00 PM
  8. Fatherland — Friday 5:30pm · Downtown
  9. Love is the monster — Friday 2:30pm · Downtown
  10. Shorts: Black Perspectives — Friday 7:15pm · 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.