Stumblday's hand-checked ranking of the best date night in Chicago the weekend of Sep 25–27, 2026: 16 picks, refreshed weekly.
16 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.
United Center, 1901 W Madison, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsTeddy Swims brings his romantic confessionals and big pop hooks to the United Center, with Mac Ayres and MarcLo.
United Center, 1901 W Madison, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsTeddy Swims brings his romantic confessionals and big pop hooks to the United Center, with Mac Ayres and MarcLo.
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsA Stranger Has No Eyes closes CUFF with a world premiere and a conversation with director C.S. Nicholson.
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsA Stranger Has No Eyes closes CUFF with a world premiere and a conversation with director C.S. Nicholson.
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.
Riviera Theatre, Andersonville, Uptown & Lincoln SquarePaul R. Burley · CC BY-SA 4.0 · Wikimedia CommonsMichael Shannon, Jason Narducy and friends play R.E.M.’s Lifes Rich Pageant at the Riviera.
Riviera Theatre, Andersonville, Uptown & Lincoln SquarePaul R. Burley · CC BY-SA 4.0 · Wikimedia CommonsMichael Shannon, Jason Narducy and friends play R.E.M.’s Lifes Rich Pageant at the Riviera.
Credit Union 1 Amphitheatre, Far SuburbsBryson Tiller brings the trap-R&B sound behind “Don’t” and Trapsoul to Tinley Park on The Neo Trapsoul Tour.
Credit Union 1 Amphitheatre, Far SuburbsBryson Tiller brings the trap-R&B sound behind “Don’t” and Trapsoul to Tinley Park on The Neo Trapsoul Tour.
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.
George Van Dusen Theatre at North Shore Center, 9501 Skokie Blvd, Evanston & Oak ParkMusic of the Baroque pairs Mozart’s final symphonies with his last piano concerto in Mozart’s Summit.
George Van Dusen Theatre at North Shore Center, 9501 Skokie Blvd, Evanston & Oak ParkMusic of the Baroque pairs Mozart’s final symphonies with his last piano concerto in Mozart’s Summit.
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.
The Newport Theater, Lincoln Park, Lakeview & WrigleyvilleEder Montes · CC BY 3.0 · Wikimedia CommonsHoneybee Rose leads a burlesque bill at Newport Theater, hosted by Hummingbird and Gaybriel Le Fae.
The Newport Theater, Lincoln Park, Lakeview & WrigleyvilleEder Montes · CC BY 3.0 · Wikimedia CommonsHoneybee Rose leads a burlesque bill at Newport Theater, hosted by Hummingbird and Gaybriel Le Fae.
