Date night in Chicago Halloween Weekend 2026

Oct 30 – Nov 1 · 55 picks hand‑checked by Stumblday against organizer pages · updated Nov 2

The 10 best date night picks in 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. Dead Girl's Quinceañera — September 26 – November 1 · Owen Theatre
  3. Topdog/Underdog — Fri, Oct 30 7:30pm · Lincoln Park
  4. Theater of the Mind — Fri, Nov 13 · Tickets from $69 · Downtown
  5. Kokandy Productions Jekyll & Hyde (Chicago) — Fri, Oct 30 7:00pm · Downtown
  6. Vladimir — Fri, Nov 13 7:30pm · Tickets $20–$60 · Lincoln Park
  7. Baby Wants Candy! The Original Completely Improvised Musical — Sat, Nov 14 7:30pm · $25 · Lincoln Park
  8. Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire” — Fri, Oct 30 7:30pm · $12 – $40 · Logan Square
  9. Oil Lamp Theater Presents “Dial M for Murder” — Fri, Oct 30 7:30pm · $55 · Oil Lamp Theater
  10. The Séance: Live (and dead) in Chicago — Sat, Oct 31 7:00pm · $40 · Stars and Garters Theater

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About this list

Stumblday's hand-checked ranking of the best date night in Chicago over Halloween weekend 2026 (Oct 30 – Nov 1): 55 picks, refreshed weekly.

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