Date night in Chicago the Weekend of Nov 20–22, 2026

Nov 20–22 · 26 picks hand‑checked by Stumblday against organizer pages · updated Nov 2

The 10 best date night picks in Chicago the weekend of Nov 20–22

  1. The Beloved Holiday Classic, “Ruth Page’s The Nutcracker,” Celebrates 60 Years with a Special One-Hour Version at Beverly Arts Center — Sat, Nov 21 1:00pm · $17 – $59 · Beverly Arts Center of Chicago
  2. Oil Lamp Theater Presents “It’s A Wonderful Life: A Live Radio Play” — Fri, Nov 20 7:30pm · $30 – $55 · Oil Lamp Theater
  3. Porchlight Music Theatre’s Little Shop of Horrors — Fri, Nov 20 7:30pm · $28 · Victory Gardens Biograph Theater
  4. The Weight — Saturday 7pm · Lincoln Park
  5. A Christmas Carol — Fri, Nov 20 7:30pm · Downtown
  6. The Deep End — Sun, Nov 22 3:00pm · $12 · Logan Square
  7. Baise-moi — Friday 8:45pm · Lincoln Park
  8. A Midsummer Night's Dream — Fri, Nov 20 7:00pm · Downtown
  9. Pat Tomasulo — Fri, Nov 20 7:00pm · Downtown
  10. Prospa present Prophecy — Fri, Nov 20 10:00pm · Downtown

More picks for Nov 20–22, 2026

Planning ahead for Nov 20–22, 2026?

It lands the Friday before, plus every Friday until then. Unsubscribe anytime.

About this list

Stumblday's hand-checked ranking of the best date night in Chicago the weekend of Nov 20–22, 2026: 26 picks, refreshed weekly.

More this weekend across Chicago