Things to Do in West Loop, Chicago the Weekend of Oct 23–25, 2026

Oct 23–25 · 61 picks hand‑checked by Stumblday against organizer pages · updated Oct 6

The 10 best things to do in West Loop, Chicago the weekend of Oct 23–25

  1. Kowalski — September 15 – October 25 · Downtown
  2. American Prophets: Writers, Religion, and Culture — Fri, Oct 23 10:00am · Downtown
  3. Oktoberfest Nation Chicago — Sep 17–Oct 24; select days · Downtown
  4. Jekyll& Hyde — Fri, Oct 23 7:00pm · Downtown
  5. Mini Zoom Room — Fri, Oct 23 10:00am · Downtown
  6. NoMI Gallery — Fri, Oct 23 · Downtown
  7. Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour — Fri, Oct 23 4:00pm · Downtown
  8. Drunk Shakespeare: Drunk Dracula (21+ Event) — Fri, Oct 23 7:00pm · Downtown
  9. Theater of the Mind — Fri, Oct 23 · Downtown
  10. Flyway City: Architecture for a Flourishing Ecosystem — Fri, Oct 23 10:00am · Downtown

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About this list

Stumblday's hand-checked ranking of the best things to do in West Loop, Chicago, Downtown, the Loop & West Loop the weekend of Oct 23–25, 2026: 61 picks.

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