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Date night in Lakeview, Chicago Halloween Weekend 2026

Oct 30 – Nov 1 · 11 picks hand‑checked by Stumblday against organizer pages · updated Nov 2

The 10 best date night picks in Lakeview, Chicago over Halloween Weekend (Oct 30 – Nov 1)

  1. Music Box of Horrors: The Final Chapter — October 1–31; horror screenings most nights · Most screenings $13 ($10 Musi… · Lakeview
  2. Topdog/Underdog — Fri, Oct 30 7:30pm · Lincoln Park
  3. Vladimir — Fri, Nov 13 7:30pm · Tickets $20–$60 · Lincoln Park
  4. Baby Wants Candy! The Original Completely Improvised Musical — Sat, Nov 14 7:30pm · $25 · Lincoln Park
  5. The Second City's: Pandemonium, Please Hold — Fri, Nov 13 6:30pm · Lincoln Park
  6. Saturday Night Sketch — Sat, Nov 14 7:30pm · $25 · Lincoln Park
  7. Kohl’s Cash: Tgif (That’s Good Improv Friday) — Fri, Nov 13 9:30pm · $15 · Lincoln Park
  8. Marquee: Musical Improv — Sun, Nov 15 6:00pm · $15 · Lincoln Park
  9. Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear” — Fri, Nov 13 7:30pm · $28 – $37 · Lincoln Park
  10. “The Last Word,” an Adventure Screenplay with a Cocktail Experience — Fri, Oct 30 7:30pm · $20 – $50 · Lincoln Park

More this weekend

About this list

Stumblday's hand-checked ranking of the best date night in Lakeview, Chicago, Lincoln Park, Lakeview & Wrigleyville over Halloween weekend 2026 (Oct 30 – Nov 1): 11 picks.

More this weekend across Chicago

Haunted Halsted Fest and Halloween ParadeNorth Halsted Street, Northalsted, Lincoln Park, Lakeview & Wrigleyville
Xempasúchil: Día de los Muertos en la Calle 2626th Street corridor, Little Village, Pilsen, West Town & the West Side
TaanTaan, Humboldt Park, Pilsen, West Town & the West Side
Fall FestLincoln Park Zoo, Lincoln Park
Dead Girl's QuinceañeraGoodman Theatre, Owen Theatre, The Loop
Jack's Pumpkin Pop-UpJack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West Loop