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Date night in Chicago on Saturday, Nov 14

Saturday, Nov 14 · 48 picks hand‑checked by Stumblday against organizer pages · 1 free in the top 10 · updated Oct 28

The 10 best date night picks in Chicago on Saturday, Nov 14

  1. The Factory Theater Presents the World Premiere of “Radical Futures” — Fri, Nov 13 7:30pm · $30 · The Factory Theater
  2. Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear” — Fri, Nov 13 7:30pm · $28 – $37 · Lincoln Park
  3. Premonitions Inc. at Kermess — Runs through Nov 15 · Kermess
  4. Comedy Hour at Annoyance Theatre — Runs through Nov 13 · Free · Annoyance Theatre & Bar
  5. Vladimir — Fri, Nov 13 7:30pm · Lincoln Park
  6. Baby Wants Candy! The Original Completely Improvised Musical — Sat, Nov 14 7:30pm · $25 · Lincoln Park
  7. Voila: The Improvised Musical — Fri, Nov 13 10:00pm · $15 · IL 60642
  8. King Hedley II — Fri, Nov 13 7:30pm · $40.00 · Andersonville
  9. Remy Bumppo Theatre Company Presents “Mud Row” — Fri, Nov 13 7:30pm · $34 – $55 · Lincoln Park
  10. Rising Stars Burlesque Revue — Fri, Nov 13 10:00pm · Stars and Garters Theater

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About this list

Stumblday's hand-checked ranking of the best date night in Chicago on Saturday, Nov 14: 48 picks, refreshed weekly.

More this weekend across Chicago

ART on THE MartChicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West Loop
Lightscape at Chicago Botanic GardenFar Suburbs
The Oracle of Evergreen: A Black Plant IT Exhibition 2026Garfield Park Conservatory, East Garfield Park, Pilsen, West Town & the West Side
Illumination: Tree Lights at The Morton ArboretumFar Suburbs
312 Comedy Festival 2026Downtown, the Loop & West Loop
“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire”Harold Washington Library Center