Date night in Evanston & Oak Park Columbus Day Weekend 2026

Hand-picked every week — checked against organizers’ own pages.

Stumblday's hand-checked ranking of the best date night in Evanston & Oak Park over Columbus Day weekend 2026 (Oct 10–12): 2 picks, refreshed weekly.

2 picks · checked Oct 6

The 2 picks

Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM

9501 Skokie Blvd, Evanston & Oak Park

Music Theater Works stages Escape to Margaritaville at the North Shore Center.

One Weekend Only

Submitted byStumblday Editors

#1Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM · One Weekend Only

One Weekend Only

Music Theater Works stages Escape to Margaritaville at the North Shore Center.

September 9 – October 25, 2026 (extended)Ticketed

Northlight Theatre, Evanston

The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.

Limited Run

Submitted byStumblday Editors

#2September 9 – October 25, 2026 (extended) · Limited Run

TicketedLimited Run

The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.