Things to Do in Wicker Park, Chicago Columbus Day Weekend 2026

Oct 9–12 · 10 picks hand‑checked by Stumblday against organizer pages · 3 free in the top 10 · updated Oct 6

The 10 best things to do in Wicker Park, Chicago over Columbus Day Weekend (Oct 9–12)

  1. Chicago Latino Dance Festival at Humboldt — Sunday, October 11, 3:00–5:00 PM · Free · Logan Square
  2. Interpol – 2026 North American Tour — Sun, Oct 11 7:00pm · Logan Square
  3. Muna – Gets So Hot Tour — Fri, Oct 9 7:00pm · Logan Square
  4. Tito Nieves - 50 Años La Historia Continua — Fri, Oct 9 8:00pm · Logan Square
  5. Transilience: Chicago Trans Pride Festival at Eckhart — Friday, October 9, 5:00–7:00 PM · Free · Logan Square
  6. Stray Chef Sundays: Donald Young — Sun, Oct 11, from 5pm until sold out · Wicker Park
  7. Phil Hanley — Fri, Oct 9 7:15pm · Logan Square
  8. Balloon Museum: EmotionAir – Art You Can Feel — Timed-entry sessions through January 19 · Logan Square
  9. Wicker Park Farmers Market — Sep 20–Oct 18, 2026 · Wicker Park
  10. Apple Bottoms x Chicago — Friday, October 9, 6:00–9:00 PM · Free · Wicker Park

About this list

Stumblday's hand-checked ranking of the best things to do in Wicker Park, Chicago, Logan Square, Wicker Park & Bucktown over Columbus Day weekend 2026 (Oct 10–12): 10 picks.

More this weekend across Chicago