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Date night in Oak Park, Chicago the Weekend of Oct 23–25, 2026

Oct 23–25 · 4 picks hand‑checked by Stumblday against organizer pages · updated Oct 6

The 4 best date night picks in Oak Park, Chicago the weekend of Oct 23–25

  1. Bill Blagg — Sun, Oct 25 2:00pm · 9501 Skokie Blvd
  2. Maria Bamford — Sat, Oct 24 8:00pm · 9501 Skokie Blvd
  3. Lions on Jeeps — Sun, Oct 25 7:00pm · 9501 Skokie Blvd
  4. Music Theater Works Presents: Escape to Margaritaville — Fri, Oct 23 7:30pm · 9501 Skokie Blvd

About this list

Stumblday's hand-checked ranking of the best date night in Oak Park, Chicago, Evanston & Oak Park the weekend of Oct 23–25, 2026: 4 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