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

Oct 23–25 · 6 picks hand‑checked by Stumblday against organizer pages · 2 free in the top 6 · updated Oct 6

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

  1. Wicker Park Farmers Market — Sun, Oct 25 8:00am · Free · Wicker Park
  2. Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire” — Fri, Oct 23 7:30pm · $12 – $40 · Logan Square
  3. Meet Me on Milwaukee (MMoM) — Sun, Oct 25 10:00am · Free · Logan Square
  4. This Wild Life w/ Nate Bergman — Fri, Oct 23 6:00pm · Logan Square
  5. Balloon Museum — Sat, Sep 12 10:00am · Logan Square
  6. Yousuke Yukimatsu — Fri, Oct 23 12:00pm · Logan Square

About this list

Stumblday's hand-checked ranking of the best things to do in Wicker Park, Chicago, Logan Square, Wicker Park & Bucktown 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
Comedy Hour at Annoyance TheatreAnnoyance Theatre & Bar
American Prophets: Writers, Religion, and CultureAmerican Writers Museum, Downtown, the Loop & West Loop
Topdog/UnderdogSteppenwolf Downstairs Theater, Lincoln Park, Lakeview & Wrigleyville