Stumblday's hand-checked ranking of the best date night in Chicago the weekend of Sep 25–27, 2026: 101 picks, refreshed weekly.
101 picks · checked Sep 21
Multiple Hyde Park venues, Hyde Park, Bronzeville & the South SideJoe Passe · CC BY-SA 2.0 · 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 SideJoe Passe · CC BY-SA 2.0 · Wikimedia CommonsHear Chicago jazz across neighborhood stages, with an anniversary band, intimate sets and a late solo performance by Joshua Redman.
Add to calendar
Harris Theater Rooftop, Downtown, the Loop & West LoopChicago 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 LoopChicago Gourmet pairs its chef-led festival with a dance-inspired theme, including events at the Harris Theater Rooftop.
Add to calendar
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Add to calendar
Arie Crown Theater, Downtown, the Loop & West LoopLegendary comedian and actor Martin Lawrence plays one night live at Arie Crown Theater.
Arie Crown Theater, Downtown, the Loop & West LoopLegendary comedian and actor Martin Lawrence plays one night live at Arie Crown Theater.
Add to calendarFriday at 5pm, one email. Unsubscribe anytime.
Lyric Opera House, Loop, Downtown, the Loop & West LoopThe Joffrey Ballet brings Molnár's Liliom to the Lyric stage for select September performances.
Lyric Opera House, Loop, Downtown, the Loop & West LoopThe Joffrey Ballet brings Molnár's Liliom to the Lyric stage for select September performances.
Add to calendar
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.
Add to calendarBassem Youssef brings his comedy tour to The Chicago Theatre for one night only.
Bassem Youssef brings his comedy tour to The Chicago Theatre for one night only.
Add to calendar
Landmark Century Centre Cinema, Lakeview, Lincoln Park, Lakeview & WrigleyvilleRxLyon · CC BY-SA 4.0 · Wikimedia CommonsOne of the world's longest-running LGBTQ+ film festivals, with new features and documentaries.
Landmark Century Centre Cinema, Lakeview, Lincoln Park, Lakeview & WrigleyvilleRxLyon · CC BY-SA 4.0 · Wikimedia CommonsOne of the world's longest-running LGBTQ+ film festivals, with new features and documentaries.
Add to calendar
Goodman Albert Theatre, Downtown, the Loop & West LoopMichel Curi · CC BY 2.0 · Wikimedia CommonsThe 7 Fingers turn a former trapezist's memoir into daring aerial theater, running into October.
Goodman Albert Theatre, Downtown, the Loop & West LoopMichel Curi · CC BY 2.0 · Wikimedia CommonsThe 7 Fingers turn a former trapezist's memoir into daring aerial theater, running into October.
Add to calendar
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopA new play runs select dates at Chicago Shakespeare's Navy Pier stage.
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopA new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Add to calendarKokandy Productions stages the Jekyll & Hyde musical at the Broadway Playhouse at Water Tower Place.
Kokandy Productions stages the Jekyll & Hyde musical at the Broadway Playhouse at Water Tower Place.
Add to calendar
Gene Siskel Film Center, the Loop, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsThe Underground Film Festival closes out with A Stranger HAS NO Eyes at Siskel.
Gene Siskel Film Center, the Loop, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsThe Underground Film Festival closes out with A Stranger HAS NO Eyes at Siskel.
Add to calendar
The Chicago Theatre, Downtown, the Loop & West LoopLaura Ramoso brings The Calm Down Tour to The Chicago Theatre.
The Chicago Theatre, Downtown, the Loop & West LoopLaura Ramoso brings The Calm Down Tour to The Chicago Theatre.
Add to calendar
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopThree friends investigate a classmate’s quinceañera disappearance in this comic thriller.
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopThree friends investigate a classmate’s quinceañera disappearance in this comic thriller.
Add to calendar
Definition Theatre (Definition @ 55th), Hyde Park, Bronzeville & the South SideRap battles, turntables and notebooks drive this final weekend at Definition Theatre.
Definition Theatre (Definition @ 55th), Hyde Park, Bronzeville & the South SideRap battles, turntables and notebooks drive this final weekend at Definition Theatre.
Add to calendar
Northlight Theatre, Evanston, Evanston & Oak ParkThe classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Northlight Theatre, Evanston, Evanston & Oak ParkThe classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Add to calendar
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsBuddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsBuddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Add to calendar
Wagner Stage, Hyde Park, Bronzeville & the South SideMarquis Hill, Makaya McCraven, Junius Paul and Joel Ross reunite for the festival's 20th.
Wagner Stage, Hyde Park, Bronzeville & the South SideMarquis Hill, Makaya McCraven, Junius Paul and Joel Ross reunite for the festival's 20th.
Add to calendar
Harris Theater Rooftop, the Loop, Downtown, the Loop & West LoopAcclaimed chefs, winemakers and mixologists pair luxury bites and pours in two rooftop sessions.
Harris Theater Rooftop, the Loop, Downtown, the Loop & West LoopAcclaimed chefs, winemakers and mixologists pair luxury bites and pours in two rooftop sessions.
Add to calendar
Harris Theater Rooftop, the Loop, Downtown, the Loop & West LoopArt Smith and Erick Williams host a Southern-style rooftop brunch with cocktails.
Harris Theater Rooftop, the Loop, Downtown, the Loop & West LoopArt Smith and Erick Williams host a Southern-style rooftop brunch with cocktails.
Add to calendar
Chicago Improv - Schaumburg, Schaumburg, Far SuburbsFrank Caliendo brings his rapid-fire sports and celebrity impressions to three Schaumburg shows.
Chicago Improv - Schaumburg, Schaumburg, Far SuburbsFrank Caliendo brings his rapid-fire sports and celebrity impressions to three Schaumburg shows.
Add to calendar
Arcada Theatre, St. Charles, Far SuburbsRonnie Marmo channels Lenny Bruce in a Joe Mantegna-directed solo show at the Arcada.
Arcada Theatre, St. Charles, Far SuburbsRonnie Marmo channels Lenny Bruce in a Joe Mantegna-directed solo show at the Arcada.
Add to calendar
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleJohn Wilson's new documentary turns concrete into a funny, personal portrait of New York.
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleJohn Wilson's new documentary turns concrete into a funny, personal portrait of New York.
Add to calendar
Graver Park, Washington Heights, Hyde Park, Bronzeville & the South SideFree circus theater brings clowning, aerial work and a story of polarization to Graver Park.
Graver Park, Washington Heights, Hyde Park, Bronzeville & the South SideFree circus theater brings clowning, aerial work and a story of polarization to Graver Park.
Add to calendar