Outdoors in Chicago Sunday Night, Columbus Day Weekend 2026

Sunday night, Oct 11 · 7 picks hand‑checked by Stumblday against organizer pages · 2 free in the top 7 · updated Oct 6

The 7 best outdoor picks in Chicago on Sunday night, Oct 11

  1. Chicago Latino Dance Festival at Humboldt — Sunday, October 11, 3:00–5:00 PM · Free · Logan Square
  2. Lincoln Park Wine Fest — October 9–11; Friday 5–10pm · General admission from $30 · Lincoln Park
  3. Night of 1,000 Jack-o'-Lanterns — October 7–11, 14–18 and 21–25, 6:30–10:30 PM · Adults from $24 for nonmember… · Glencoe
  4. Play On! — Chicago Shakespeare Theater — September 11–October 18; selected performances · Downtown
  5. teamLab & Allison Martino in Conversation — Sunday, October 11 4–5 PM · Free · Hyde Park
  6. Kanan Gill: Not This Again — Sun, Oct 11 7:00pm · Lincoln Park
  7. Stray Chef Sundays: Donald Young — Sun, Oct 11, from 5pm until sold out · Wicker Park

About this list

Stumblday's hand-checked ranking of the best outdoors in Chicago on Sunday night of Columbus Day weekend, Oct 11: 7 picks, refreshed weekly.

More this weekend across Chicago