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Date night in Wrigleyville, Chicago the Weekend of Oct 30–Nov 1, 2026

Oct 30 – Nov 1 · 10 picks hand‑checked by Stumblday against organizer pages · updated Oct 13

The 10 best date night picks in Wrigleyville, Chicago the weekend of Oct 30 – Nov 1

  1. Topdog/Underdog — Fri, Oct 30 7:30pm · Lincoln Park
  2. Vladimir — Fri, Oct 30 7:30pm · Lincoln Park
  3. Baby Wants Candy! The Original Completely Improvised Musical — Sat, Oct 31 7:30pm · $25 · Lincoln Park
  4. The Second City's: Pandemonium, Please Hold — Fri, Oct 30 6:30pm · Lincoln Park
  5. Saturday Night Sketch — Sat, Oct 31 7:30pm · $25 · Lincoln Park
  6. Kohl’s Cash: Tgif (That’s Good Improv Friday) — Fri, Oct 30 9:30pm · $15 · Lincoln Park
  7. Marquee: Musical Improv — Sun, Nov 1 6:00pm · $15 · Lincoln Park
  8. Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear” — Fri, Oct 30 7:30pm · $28 – $37 · Lincoln Park
  9. “The Last Word,” an Adventure Screenplay with a Cocktail Experience — Fri, Oct 30 7:30pm · $20 – $50 · Lincoln Park
  10. Remy Bumppo Theatre Company Presents “Mud Row” — Fri, Oct 30 7:30pm · $34 – $55 · Lincoln Park

About this list

Stumblday's hand-checked ranking of the best date night in Wrigleyville, Chicago, Lincoln Park, Lakeview & Wrigleyville the weekend of Oct 30–Nov 1, 2026: 10 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 Fest at Lincoln Park ZooLincoln Park Zoo, Lincoln Park, Lakeview & Wrigleyville
Music Box of Horrors: The Final ChapterMusic Box Theatre, Lakeview
Dead Girl's QuinceañeraGoodman Theatre, Owen Theatre, The Loop