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

Oct 23–25 · 11 picks hand‑checked by Stumblday against organizer pages · updated Oct 6

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

  1. Northwestern vs Rutgers and The Great Chicago Food Festival — Sat, Oct 24 · 1501 Central
  2. Bill Blagg — Sun, Oct 25 2:00pm · 9501 Skokie Blvd
  3. Great Food Expo — Sat, Oct 24 through Sun, Oct 25, 2026 · Rosemont
  4. Chicago Stars FC vs. Houston Dash — Fri, Oct 23 7:00pm · 2235 N Campus Dr
  5. Maria Bamford — Sat, Oct 24 8:00pm · 9501 Skokie Blvd
  6. The Block Collects 2026 — On view through Dec 6 · Evanston & Oak Park
  7. Picturing the Modern Metropolis: Prints and Photographs — On view through Dec 6 · Evanston & Oak Park
  8. La Diosa — Fri, Oct 23 8:00pm · 9501 Skokie Blvd
  9. Lions on Jeeps — Sun, Oct 25 7:00pm · 9501 Skokie Blvd
  10. Music Theater Works Presents: Escape to Margaritaville — Fri, Oct 23 7:30pm · 9501 Skokie Blvd

More picks for Oct 23–25, 2026

About this list

Stumblday's hand-checked ranking of the best things to do in Oak Park, Chicago, Evanston & Oak Park the weekend of Oct 23–25, 2026: 11 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