Stumblday's hand-checked ranking of the best date night in Chicago on Saturday, Sep 26: 10 picks, refreshed weekly.
10 picks · checked Sep 10
Harris Theater Rooftop, Downtown, the Loop & West LoopChristine Harrison Frei · CC BY-SA 4.0 · Wikimedia CommonsChicago Gourmet pairs its chef-led festival with a dance-inspired theme, including events at the Harris Theater Rooftop.
Harris Theater Rooftop, Downtown, the Loop & West LoopChristine Harrison Frei · CC BY-SA 4.0 · Wikimedia CommonsChicago Gourmet pairs its chef-led festival with a dance-inspired theme, including events at the Harris Theater Rooftop.
Multiple Hyde Park venues, Hyde Park, Bronzeville & the South SideTizmsound · CC BY-SA 3.0 · Wikimedia CommonsHear Chicago jazz across neighborhood stages, with an anniversary band, intimate sets and a late solo performance by Joshua Redman.
Multiple Hyde Park venues, Hyde Park, Bronzeville & the South SideTizmsound · CC BY-SA 3.0 · Wikimedia CommonsHear Chicago jazz across neighborhood stages, with an anniversary band, intimate sets and a late solo performance by Joshua Redman.
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsSibelius’s Seventh and Shostakovich’s Fourth meet in a two-symphony CSO program led by Klaus Mäkelä.
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsSibelius’s Seventh and Shostakovich’s Fourth meet in a two-symphony CSO program led by Klaus Mäkelä.
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!
Rosemont Theatre, Evanston & Oak ParkZol87 from Chicago, Illinois, USA · CC BY-SA 4.0 · Wikimedia CommonsJuanes brings his 2026 world tour to Rosemont Theatre, with the JuanesTeban album shaping the tour’s context.
Rosemont Theatre, Evanston & Oak ParkZol87 from Chicago, Illinois, USA · CC BY-SA 4.0 · Wikimedia CommonsJuanes brings his 2026 world tour to Rosemont Theatre, with the JuanesTeban album shaping the tour’s context.
Chicago Theater Works, Lincoln Park, Lakeview & WrigleyvilleLoew, Inc. · Public domain · Wikimedia CommonsExplore sustainable fashion through a runway show, designer conversations and a symposium offered in a day-pass bundle.
Chicago Theater Works, Lincoln Park, Lakeview & WrigleyvilleLoew, Inc. · Public domain · Wikimedia CommonsExplore sustainable fashion through a runway show, designer conversations and a symposium offered in a day-pass bundle.
Facets, Lincoln Park, Lakeview & WrigleyvilleShort films from emerging and established filmmakers share the screen at Aladerri International Film Festival at FACETS.
Facets, Lincoln Park, Lakeview & WrigleyvilleShort films from emerging and established filmmakers share the screen at Aladerri International Film Festival at FACETS.
Huntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopDwightSchruteDunderMifflin · CC BY 4.0 · Wikimedia CommonsFoster the People’s indie pop meets a stage world of unraveling 1950s optimism at Northerly Island, with Goth Babe.
Huntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopDwightSchruteDunderMifflin · CC BY 4.0 · Wikimedia CommonsFoster the People’s indie pop meets a stage world of unraveling 1950s optimism at Northerly Island, with Goth Babe.
Auditorium Theatre, Downtown, the Loop & West LoopCervin Robinson, photographer. · Public domain · Wikimedia CommonsThe Chicago Philharmonic plays the score live as Top Gun: Maverick fills the Auditorium screen.
Auditorium Theatre, Downtown, the Loop & West LoopCervin Robinson, photographer. · Public domain · Wikimedia CommonsThe Chicago Philharmonic plays the score live as Top Gun: Maverick fills the Auditorium screen.
