#1
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Sep 25, 2026 · 7:30pm
Topdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Limited Run
Date night in Wrigleyville, Chicago the Weekend of Sep 25–27, 2026
Stumblday's hand-checked ranking of the best date night in Wrigleyville, Chicago, Lincoln Park, Lakeview & Wrigleyville the weekend of Sep 25–27, 2026: 43 picks.
43 picks · checked Sep 21
43 picks
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & Wrigleyville#1Fri, Sep 25, 2026 · 7:30pm · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Add to calendar#2
Landmark Century Centre Cinema, Lakeview, Lincoln Park, Lakeview & WrigleyvilleRxLyon · CC BY-SA 4.0 · Wikimedia CommonsSeptember 17–27, 2026; screening times vary$15 general admission ($13 me…
Reeling 2026: The 44th Chicago LGBTQ+ International Film Festival
One of the world's longest-running LGBTQ+ film festivals, with new features and documentaries.
Limited Run
#2September 17–27, 2026; screening times vary · Limited Run
Landmark Century Centre Cinema, Lakeview, Lincoln Park, Lakeview & WrigleyvilleRxLyon · CC BY-SA 4.0 · Wikimedia CommonsReeling 2026: The 44th Chicago LGBTQ+ International Film Festival
One of the world's longest-running LGBTQ+ film festivals, with new features and documentaries.
Add to calendar#3
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSeptember 25–27, 2026; four screenings daily, with the last Sunday show at 9:30 p.m.Ticketed via Music Box Theatre
The History of Concrete — Opening Weekend
John Wilson's new documentary turns concrete into a funny, personal portrait of New York.
One Weekend Only
#3September 25–27, 2026; four screenings daily, with the last Sunday show at 9:30 p.m. · One Weekend Only
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleThe History of Concrete — Opening Weekend
John Wilson's new documentary turns concrete into a funny, personal portrait of New York.
Add to calendar#4
The Second City, Lincoln Park, Lakeview & WrigleyvilleFri, Sep 25, 2026 · 8:00pm
Best of The Second City
Second City revisits sketches and songs from its archive, updated alongside newer material.
One Weekend Only
#4Fri, Sep 25, 2026 · 8:00pm · One Weekend Only
The Second City, Lincoln Park, Lakeview & WrigleyvilleBest of The Second City
Second City revisits sketches and songs from its archive, updated alongside newer material.
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#5
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSaturday, September 26, 2026, 11:59 p.m.Ticketed via the Music Box Th…
The Rocky Horror Picture Show in 35mm with Shadowcast
The Rocky Horror Picture Show in 35mm with Shadowcast has enough weekend energy to earn a spot on the board.
Limited Run
#5Saturday, September 26, 2026, 11:59 p.m. · Limited Run
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleThe Rocky Horror Picture Show in 35mm with Shadowcast
The Rocky Horror Picture Show in 35mm with Shadowcast has enough weekend energy to earn a spot on the board.
Add to calendar#6
Park West, Lincoln Park, Lakeview & WrigleyvilleSat, Sep 26, 2026 · 7:30pm
Crashing Out Live – Chicago, IL – 2026 Tour
Philip DeFranco and Alex Pearlman take their Crashing Out comedy tour to Park West.
One Day Only
#6Sat, Sep 26, 2026 · 7:30pm · One Day Only
Park West, Lincoln Park, Lakeview & WrigleyvilleCrashing Out Live – Chicago, IL – 2026 Tour
Philip DeFranco and Alex Pearlman take their Crashing Out comedy tour to Park West.
Add to calendar#7
Facets, Lincoln Park, Lakeview & WrigleyvilleThrough Sep 27, 2026
Aladerri International Film Festival
Short films from emerging and established filmmakers share the screen at Aladerri International Film Festival at FACETS.
One Weekend Only
#7Through Sep 27, 2026 · One Weekend Only
Facets, Lincoln Park, Lakeview & WrigleyvilleAladerri International Film Festival
Short films from emerging and established filmmakers share the screen at Aladerri International Film Festival at FACETS.
Add to calendar#8
The Second City, Lincoln Park, Lakeview & WrigleyvilleSat, Sep 26, 2026 · 7:30pm$25
Baby Wants Candy! The Original Completely Improvised Musical
Baby Wants Candy! The Original Completely Improvised Musical has enough weekend energy to earn a spot on the board.
One Day Only
#8Sat, Sep 26, 2026 · 7:30pm · One Day Only
The Second City, Lincoln Park, Lakeview & WrigleyvilleBaby Wants Candy! The Original Completely Improvised Musical
Baby Wants Candy! The Original Completely Improvised Musical has enough weekend energy to earn a spot on the board.
Add to calendar#9
Sat, Sep 26, 2026 · 7:30pm
Jazz Is Dead Presents - Cortex (18+)
Jazz Is Dead brings Cortex to the Vic Theatre for one 18-and-over night.
Limited Run
#9Sat, Sep 26, 2026 · 7:30pm · Limited Run
Jazz Is Dead Presents - Cortex (18+)
Jazz Is Dead brings Cortex to the Vic Theatre for one 18-and-over night.
Add to calendar#10
Greenhouse Theater Center, Lincoln Park, Lakeview & WrigleyvilleSat, Sep 26, 2026 · 11:00am
If You Give a Mouse a Cookie
If You Give a Mouse a Cookie has enough weekend energy to earn a spot on the board.
One Day Only
#10Sat, Sep 26, 2026 · 11:00am · One Day Only
Greenhouse Theater Center, Lincoln Park, Lakeview & WrigleyvilleIf You Give a Mouse a Cookie
If You Give a Mouse a Cookie has enough weekend energy to earn a spot on the board.
Add to calendar#11
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleFri, Sep 25, 2026 · 7:00pm
Muses
Muses has enough weekend energy to earn a spot on the board.
One Weekend Only
#11Fri, Sep 25, 2026 · 7:00pm · One Weekend Only
Theater Wit, Lincoln Park, Lakeview & Wrigleyville#12
Mrs. Murphy & Sons Irish Bistro, Lincoln Park, Lakeview & WrigleyvilleFri, Sep 25, 2026 · 7:00pm$20
Romeo & Juliet
Romeo & Juliet has enough weekend energy to earn a spot on the board.
One Day Only
#12Fri, Sep 25, 2026 · 7:00pm · One Day Only
Mrs. Murphy & Sons Irish Bistro, Lincoln Park, Lakeview & Wrigleyville#13
Chicago Theater Works, Lincoln Park, Lakeview & WrigleyvilleSat, Sep 26, 2026 · 1:00pm$75
Sustainable Fashion Week Symposium & Runway
Explore sustainable fashion through a runway show, designer conversations and a symposium offered in a day-pass bundle.
One Day Only
#13Sat, Sep 26, 2026 · 1:00pm · One Day Only
Chicago Theater Works, Lincoln Park, Lakeview & WrigleyvilleSustainable Fashion Week Symposium & Runway
Explore sustainable fashion through a runway show, designer conversations and a symposium offered in a day-pass bundle.
Add to calendar#14
The Newport Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Sep 25, 2026 · 7:00pm
The Uncanny Attic: Chapters I-L
A camp macabre series inspired by Edward Gorey's The Gashlycrumb Tinies.
One Day Only
#14Fri, Sep 25, 2026 · 7:00pm · One Day Only
The Newport Theater, Lincoln Park, Lakeview & WrigleyvilleThe Uncanny Attic: Chapters I-L
A camp macabre series inspired by Edward Gorey's The Gashlycrumb Tinies.
Add to calendar#15
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSaturday, September 26, 2026, 4:00 p.m.Ticketed via the Music Box Th…
The Harder They Come
The Harder They Come has enough weekend energy to earn a spot on the board.
Limited Run
#15Saturday, September 26, 2026, 4:00 p.m. · Limited Run
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleThe Harder They Come
The Harder They Come has enough weekend energy to earn a spot on the board.
Add to calendar#16
The Second City, Lincoln Park, Lakeview & WrigleyvilleOpen runTickets starting at $45
Pandemonium, Please Hold
The Second City's 114th Mainstage revue is a loud, fast six-person comedy show.
Limited Run
#16Open run · Limited Run
The Second City, Lincoln Park, Lakeview & WrigleyvillePandemonium, Please Hold
The Second City's 114th Mainstage revue is a loud, fast six-person comedy show.
#17
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSunday, September 27, 2026, 7:00 p.m.Ticketed via the Music Box Th…
Babylon (1980)
Babylon (1980) has enough weekend energy to earn a spot on the board.
Limited Run
#17Sunday, September 27, 2026, 7:00 p.m. · Limited Run
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & Wrigleyville#18
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleFri, Sep 25, 2026, 7:00pm CDT — Music Box Theatre
Lovers Rock
Lovers Rock has enough weekend energy to earn a spot on the board.
Limited Run
#18Fri, Sep 25, 2026, 7:00pm CDT — Music Box Theatre · Limited Run
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & Wrigleyville#19
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSat, Sep 26, 2026 · 7:30pm$22
The Best of IO
The Best of IO has enough weekend energy to earn a spot on the board.
One Day Only
#19Sat, Sep 26, 2026 · 7:30pm · One Day Only
iO Theater, Lincoln Park, Lakeview & Wrigleyville#20
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSaturday, September 26, 2026, 9:15 p.m.Ticketed via the Music Box Th…
Reggae Sunsplash
Reggae Sunsplash has enough weekend energy to earn a spot on the board.
Limited Run
#20Saturday, September 26, 2026, 9:15 p.m. · Limited Run
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleReggae Sunsplash
Reggae Sunsplash has enough weekend energy to earn a spot on the board.
Add to calendar#21
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSunday, September 27, 2026, 9:15 p.m.Ticketed via the Music Box Th…
Rockers
Rockers has enough weekend energy to earn a spot on the board.
Limited Run
#21Sunday, September 27, 2026, 9:15 p.m. · Limited Run
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & Wrigleyville#22
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSun, Sep 27, 2026 · 7:30pm$15
Harold Night
Harold Night has enough weekend energy to earn a spot on the board.
One Day Only
#22Sun, Sep 27, 2026 · 7:30pm · One Day Only
iO Theater, Lincoln Park, Lakeview & Wrigleyville#23
Stars and Garters Theater, Lincoln Park, Lakeview & WrigleyvilleSat, Sep 26, 2026 · 7:00pm$40
The Séance: Live (and dead) in Chicago
A theatrical séance recreating 19th-century spirit circles at Stars and Garters.
One Day Only
#23Sat, Sep 26, 2026 · 7:00pm · One Day Only
Stars and Garters Theater, Lincoln Park, Lakeview & WrigleyvilleThe Séance: Live (and dead) in Chicago
A theatrical séance recreating 19th-century spirit circles at Stars and Garters.
Add to calendar#24
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSat, Sep 26, 2026 · 7:30pm$25
Saturday Night Sketch
Saturday Night Sketch has enough weekend energy to earn a spot on the board.
One Day Only
#24Sat, Sep 26, 2026 · 7:30pm · One Day Only
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSaturday Night Sketch
Saturday Night Sketch has enough weekend energy to earn a spot on the board.
Add to calendar
