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

Oct 23–25 · 14 picks hand‑checked by Stumblday against organizer pages · updated Oct 6

The 10 best date night picks in Lakeview, Chicago the weekend of Oct 23–25

  1. Topdog/Underdog — Fri, Oct 23 7:30pm · Lincoln Park
  2. Baby Wants Candy! The Original Completely Improvised Musical — Sat, Oct 24 7:30pm · $25 · Lincoln Park
  3. Vladimir — Fri, Oct 23 7:30pm · Lincoln Park
  4. Marquee: Musical Improv — Sun, Oct 25 6:00pm · $15 · Lincoln Park
  5. Kohl’s Cash: Tgif (That’s Good Improv Friday) — Fri, Oct 23 9:30pm · $15 · Lincoln Park
  6. Saturday Night Sketch — Sat, Oct 24 7:30pm · $25 · Lincoln Park
  7. The Second City's: Pandemonium, Please Hold — Fri, Oct 23 6:30pm · Lincoln Park
  8. Music Box of Horrors: The Final Chapter — October 1–31; horror screenings most nights · Most screenings $13 ($10 Musi… · Lakeview
  9. Remy Bumppo Theatre Company Presents “Mud Row” — Fri, Oct 23 7:30pm · $34 – $55 · Lincoln Park
  10. Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear” — Fri, Oct 23 7:30pm · $28 – $37 · Lincoln Park

More picks for Oct 23–25, 2026

About this list

Stumblday's hand-checked ranking of the best date night in Lakeview, Chicago, Lincoln Park, Lakeview & Wrigleyville the weekend of Oct 23–25, 2026: 14 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