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

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

The 6 best things to do in Uptown, Chicago the weekend of Oct 23–25

  1. You Can't Fake the Funk — Sep 5 – Oct 25 · Uptown
  2. Kino, Kaffee und Kuchen — Sat, Oct 24 10:30am · Andersonville
  3. Antepli Mediterranean Grill — Open this weekend — recently opened · Andersonville
  4. Ela Thai Kitchen — Open this weekend — recently opened · Andersonville
  5. King Hedley II — Fri, Oct 23 7:30pm · $40.00 · Andersonville
  6. A Strange Loop — October 8 – November 8 · Andersonville

About this list

Stumblday's hand-checked ranking of the best things to do in Uptown, Chicago, Andersonville, Uptown & Lincoln Square the weekend of Oct 23–25, 2026: 6 picks.

More this weekend across Chicago

BOO! at the ZooBrookfield Zoo Chicago
Fall Fest at Lincoln Park ZooLincoln Park Zoo, Lincoln Park
KowalskiLookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West Loop
Wicker Park Farmers MarketWicker Park
Comedy Hour at Annoyance TheatreAnnoyance Theatre & Bar
American Prophets: Writers, Religion, and CultureAmerican Writers Museum, Downtown, the Loop & West Loop