Stumblday's hand-checked ranking of the best date night in Chicago the weekend of Sep 18–20, 2026: 14 picks, refreshed weekly.
14 picks · checked Sep 10
Hamilton Park and Cultural Center, Hyde Park, Bronzeville & the South SideChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia CommonsEnglewood Jazz Festival brings original music and intergenerational ensembles to Hamilton Park for its 27th edition.
Hamilton Park and Cultural Center, Hyde Park, Bronzeville & the South SideChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia CommonsEnglewood Jazz Festival brings original music and intergenerational ensembles to Hamilton Park for its 27th edition.
United Center, 1901 W Madison, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsPhoebe Bridgers brings the Lost Tour to the United Center with special guest Alex G.
United Center, 1901 W Madison, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsPhoebe Bridgers brings the Lost Tour to the United Center with special guest Alex G.
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsHilary Hahn plays Mendelssohn with the CSO, framed by Schumann and Dvořák under Petr Popelka.
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsHilary Hahn plays Mendelssohn with the CSO, framed by Schumann and Dvořák under Petr Popelka.
Garfield Park Field House. 100 N. Central Park Avenue, Chicago, IL, 60624Disabled Chicago artists and Garfield Park student composers share a free art-and-music showcase at the field house.
Garfield Park Field House. 100 N. Central Park Avenue, Chicago, IL, 60624Disabled Chicago artists and Garfield Park student composers share a free art-and-music showcase at the field house.
Lyric Opera House, Loop, Downtown, the Loop & West LoopRaymond Britt · CC BY-SA 3.0 · Wikimedia CommonsJoffrey premieres John Neumeier’s Liliom in Chicago, pairing narrative ballet with Michel Legrand’s jazz-inflected score.
Lyric Opera House, Loop, Downtown, the Loop & West LoopRaymond Britt · CC BY-SA 3.0 · Wikimedia CommonsJoffrey premieres John Neumeier’s Liliom in Chicago, pairing narrative ballet with Michel Legrand’s jazz-inflected score.
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!
Anthenaeum Theater, Lincoln Park, Lakeview & WrigleyvilleChicago Story Fest blends journalists’ stories with film, dance and live music at the Athenaeum.
Anthenaeum Theater, Lincoln Park, Lakeview & WrigleyvilleChicago Story Fest blends journalists’ stories with film, dance and live music at the Athenaeum.
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.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThe comedian behind Father and The Intruder brings The Big Bowl Tour to the Chicago Theatre: Atsuko Okatsuka, in person.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThe comedian behind Father and The Intruder brings The Big Bowl Tour to the Chicago Theatre: Atsuko Okatsuka, in person.
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvillePaul R. Burley · CC0 · Wikimedia CommonsComedy and poetry meet in ALOK’s live show at the Vic Theatre.
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvillePaul R. Burley · CC0 · Wikimedia CommonsComedy and poetry meet in ALOK’s live show at the Vic Theatre.
The Edge Theater, Andersonville, Uptown & Lincoln SquareWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsShubukai marks fifty years with Japanese classical dance, live music and guests from Hachioji Kuruma Ningyo puppet theatre.
The Edge Theater, Andersonville, Uptown & Lincoln SquareWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsShubukai marks fifty years with Japanese classical dance, live music and guests from Hachioji Kuruma Ningyo puppet theatre.
Credit Union 1 Amphitheatre, Far SuburbsTim McGraw brings the Pawn Shop Guitar Tour to Tinley Park, with Virginia country band 49 Winchester opening.
Credit Union 1 Amphitheatre, Far SuburbsTim McGraw brings the Pawn Shop Guitar Tour to Tinley Park, with Virginia country band 49 Winchester opening.
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleA would-be documentarian’s obsession curdles into menace in Tim Kasher’s Riot Fest aftershow screening at FACETS.
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleA would-be documentarian’s obsession curdles into menace in Tim Kasher’s Riot Fest aftershow screening at FACETS.
Hunter Pavilion At Ravinia, Evanston & Oak ParkTom Jones brings a catalog spanning pop hits, rhythm and blues and stripped-back roots recordings to Ravinia.
Hunter Pavilion At Ravinia, Evanston & Oak ParkTom Jones brings a catalog spanning pop hits, rhythm and blues and stripped-back roots recordings to Ravinia.
