Stumblday's hand-checked ranking of the best date night in Chicago the weekend of Sep 11–13, 2026: 13 picks, refreshed weekly.
13 picks · checked Sep 10
Goodman Albert Theatre, Downtown, the Loop & West LoopThe Goodman premieres a 7 Fingers acrobatic theater piece set inside an attic.
Goodman Albert Theatre, Downtown, the Loop & West LoopThe Goodman premieres a 7 Fingers acrobatic theater piece set inside an attic.
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopDuke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopDuke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
James M. Nederlander Theatre, 24 W Randolph, Downtown, the Loop & West LoopAaron Volkening · CC BY 2.0 · Wikimedia CommonsBaby and Johnny’s summer romance reaches the Nederlander with live music in Dirty Dancing: The Musical.
James M. Nederlander Theatre, 24 W Randolph, Downtown, the Loop & West LoopAaron Volkening · CC BY 2.0 · Wikimedia CommonsBaby and Johnny’s summer romance reaches the Nederlander with live music in Dirty Dancing: The Musical.
Hunter Pavilion At Ravinia, Evanston & Oak ParkDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsAlison Krauss and Union Station bring the Arcadia Tour to Ravinia with Jerry Douglas and guest Theo Lawrence.
Hunter Pavilion At Ravinia, Evanston & Oak ParkDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsAlison Krauss and Union Station bring the Arcadia Tour to Ravinia with Jerry Douglas and guest Theo Lawrence.
Gene Siskel Film Center, Downtown, the Loop & West LoopNgozi Onwurah’s Welcome II the Terrordome returns in a restored presentation, bringing its Afrofuturist dystopia to the Siskel.
Gene Siskel Film Center, Downtown, the Loop & West LoopNgozi Onwurah’s Welcome II the Terrordome returns in a restored presentation, bringing its Afrofuturist dystopia to the Siskel.
Rosemont Theatre, Evanston & Oak ParkMichel Curi · CC BY 2.0 · Wikimedia CommonsBinomio de Oro de América brings a fifty-year vallenato legacy, rooted in Colombia’s accordion tradition, to Rosemont Theatre.
Rosemont Theatre, Evanston & Oak ParkMichel Curi · CC BY 2.0 · Wikimedia CommonsBinomio de Oro de América brings a fifty-year vallenato legacy, rooted in Colombia’s accordion tradition, to Rosemont Theatre.
Harris Theater for Music and Dance, Downtown, the Loop & West LoopYan Da (flicker user darajan) · CC BY 2.0 · Wikimedia CommonsPhysicians trade clinics for the Harris stage in a World Doctors Orchestra concert benefiting Chicago health programs.
Harris Theater for Music and Dance, Downtown, the Loop & West LoopYan Da (flicker user darajan) · CC BY 2.0 · Wikimedia CommonsPhysicians trade clinics for the Harris stage in a World Doctors Orchestra concert benefiting Chicago health programs.
Gene Siskel Film Center, Downtown, the Loop & West LoopFollow Luis Valdez from farmworker theatre to Zoot Suit and La Bamba in American Pachuco at the Gene Siskel Film Center.
Gene Siskel Film Center, Downtown, the Loop & West LoopFollow Luis Valdez from farmworker theatre to Zoot Suit and La Bamba in American Pachuco at the Gene Siskel Film Center.
Hunter Pavilion At Ravinia, Evanston & Oak ParkNorteño mainstays Los Tigres del Norte headline Fiesta Ravinia’s tenth anniversary, with Lucía opening.
Hunter Pavilion At Ravinia, Evanston & Oak ParkNorteño mainstays Los Tigres del Norte headline Fiesta Ravinia’s tenth anniversary, with Lucía opening.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopThank You (25 Millions ) views from Fresno, USA · CC BY 2.0 · Wikimedia CommonsAdrián Uribe revisits El Vítor, Carmelo and other comic characters on the Chicago Theatre’s 50 y Pico Tour stop.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopThank You (25 Millions ) views from Fresno, USA · CC BY 2.0 · Wikimedia CommonsAdrián Uribe revisits El Vítor, Carmelo and other comic characters on the Chicago Theatre’s 50 y Pico Tour stop.
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville416th Theater Engineer Command Army Reserve · Public domain · Wikimedia CommonsAvalon Fast’s Camp brings guilt, uneasy belonging and a voice in the woods to the FACETS screen.
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville416th Theater Engineer Command Army Reserve · Public domain · Wikimedia CommonsAvalon Fast’s Camp brings guilt, uneasy belonging and a voice in the woods to the FACETS screen.
aloft circus arts, Logan Square, Wicker Park & BucktownKing of Hearts · CC BY-SA 3.0 · Wikimedia CommonsAloft Circus Arts brings The Pieces home from Edinburgh, building a one-night circus around bodies and shifting structures.
aloft circus arts, Logan Square, Wicker Park & BucktownKing of Hearts · CC BY-SA 3.0 · Wikimedia CommonsAloft Circus Arts brings The Pieces home from Edinburgh, building a one-night circus around bodies and shifting structures.
Credit Union 1 Amphitheatre, Far SuburbsDan + Shay’s Young era brings country-pop harmonies and songs about growing older to Tinley Park.
Credit Union 1 Amphitheatre, Far SuburbsDan + Shay’s Young era brings country-pop harmonies and songs about growing older to Tinley Park.
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