#1
Studio5 Performing Arts CenterFriday · Oct 16, 2026–Oct 17, 2026
All at Once — The Seldoms with Timothy Daisy
All at Once — The Seldoms with Timothy Daisy is listed for Chicago this weekend.
One Weekend Only
Date night in Chicago Friday Night, Oct 16
Hand-picked every week — checked against organizers’ own pages.
Stumblday's hand-checked ranking of the best date night in Chicago on Friday night, Oct 16: 20 picks, refreshed weekly.
20 picks · checked Sep 28
20 picks
The 10 picks
Studio5 Performing Arts Center#1Friday · Oct 16, 2026–Oct 17, 2026 · One Weekend Only
Studio5 Performing Arts CenterAll at Once — The Seldoms with Timothy Daisy
All at Once — The Seldoms with Timothy Daisy is listed for Chicago this weekend.
Add to calendar#2
Gene Siskel Film Center, Downtown, the Loop & West Loop#2Friday 8pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#3
American Writers Museum, Downtown, the Loop & West LoopFriday, October 16, 2026, 6:00 PM–8:00 PM$6 – $8
Live Reading: “Cold Was the Ground”
Live Reading: “Cold Was the Ground” is listed for Chicago this weekend.
One Day Only
#3Friday, October 16, 2026, 6:00 PM–8:00 PM · One Day Only
American Writers Museum, Downtown, the Loop & West LoopLive Reading: “Cold Was the Ground”
Live Reading: “Cold Was the Ground” is listed for Chicago this weekend.
Add to calendar#4
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleOct 16, 2026–Oct 18, 2026$34 – $55
Remy Bumppo Theatre Company Presents “Mud Row”
Remy Bumppo Theatre Company Presents “Mud Row” is listed for Chicago this weekend.
One Weekend Only
#4Oct 16, 2026–Oct 18, 2026 · One Weekend Only
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleRemy Bumppo Theatre Company Presents “Mud Row”
Remy Bumppo Theatre Company Presents “Mud Row” is listed for Chicago this weekend.
Add to calendar#5
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville#5Friday 7pm · One Day Only
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville#6
St. Agustine’s CollegeFriday · Oct 16, 2026–Oct 17, 2026
El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival
El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival is listed.
One Weekend Only
#6Friday · Oct 16, 2026–Oct 17, 2026 · One Weekend Only
St. Agustine’s CollegeEl Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival
El Evangelio Jornalero – Destinos: 9th Chicago International Latino Theater Festival is listed.
Add to calendar#7
El SchomburgFriday · Oct 16, 2026–Oct 17, 2026
Vampire Playlist – Destinos: 9th Chicago International Latino Theater Festival
Vampire Playlist – Destinos: 9th Chicago International Latino Theater Festival is listed for.
One Weekend Only
#7Friday · Oct 16, 2026–Oct 17, 2026 · One Weekend Only
El SchomburgVampire Playlist – Destinos: 9th Chicago International Latino Theater Festival
Vampire Playlist – Destinos: 9th Chicago International Latino Theater Festival is listed for.
Add to calendar#8
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleOct 16, 2026–Oct 18, 2026$28 – $37
Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear”
Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear” is listed for.
One Weekend Only
#8Oct 16, 2026–Oct 18, 2026 · One Weekend Only
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleBabes With Blades Theatre Company Presents William Shakespeare’s “King Lear”
Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear” is listed for.
Add to calendar#9
Aguijón TheaterOct 16, 2026–Oct 18, 2026
I.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival
I.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival is.
One Weekend Only
#9Oct 16, 2026–Oct 18, 2026 · One Weekend Only
Aguijón TheaterI.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival
I.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival is.
Add to calendar#10
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleFriday, October 16, 2026, 7:30 PM–9:30 PM
OFF Book: The Improvised Musical Podcast
OFF Book: The Improvised Musical Podcast is listed for Chicago this weekend.
One Day Only
#10Friday, October 16, 2026, 7:30 PM–9:30 PM · One Day Only
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleOFF Book: The Improvised Musical Podcast
OFF Book: The Improvised Musical Podcast is listed for Chicago this weekend.
Add to calendarMore picks for Oct 16–18, 2026
#11
Northwestern University Chicago Campus – Abbott Hall Wirtz TheatreFriday, October 16, 2026, 7:30 PM–9:00 PM
Takes All Kinds
Takes All Kinds is listed for Chicago this weekend.
One Day Only
#11Friday, October 16, 2026, 7:30 PM–9:00 PM · One Day Only
Northwestern University Chicago Campus – Abbott Hall Wirtz Theatre#12
Gene Siskel Film Center, Downtown, the Loop & West Loop#12Friday 5:30pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#13
The Comedy Bar, Downtown, the Loop & West LoopFriday · Oct 16, 2026–Oct 17, 2026$25 – $35
Joey Bragg at The Comedy Bar
Joey Bragg at The Comedy Bar is listed for Chicago this weekend.
One Weekend Only
#13Friday · Oct 16, 2026–Oct 17, 2026 · One Weekend Only
The Comedy Bar, Downtown, the Loop & West LoopJoey Bragg at The Comedy Bar
Joey Bragg at The Comedy Bar is listed for Chicago this weekend.
Add to calendar#14
KermessFriday · Oct 16, 2026–Oct 17, 2026
Premonitions Inc. at Kermess
Premonitions Inc. at Kermess is listed for Chicago this weekend.
One Weekend Only
#14Friday · Oct 16, 2026–Oct 17, 2026 · One Weekend Only
KermessPremonitions Inc. at Kermess
Premonitions Inc. at Kermess is listed for Chicago this weekend.
Add to calendarPlanning ahead for Oct 16–18, 2026?
It lands the Friday before, plus every Friday until then. Unsubscribe anytime.
#15
Gene Siskel Film Center, Downtown, the Loop & West LoopFriday 7:15pm
Shorts: Black Perspectives
Shorts: Black Perspectives is listed for Chicago this weekend.
Limited Run
#15Friday 7:15pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopShorts: Black Perspectives
Shorts: Black Perspectives is listed for Chicago this weekend.
Add to calendar#16
CornservatoryFriday · Oct 16, 2026–Oct 17, 2026
Death Toll: The Halloween Drinking Game Sketch Comedy Show
Death Toll: The Halloween Drinking Game Sketch Comedy Show is listed for Chicago this weekend.
One Weekend Only
#16Friday · Oct 16, 2026–Oct 17, 2026 · One Weekend Only
CornservatoryDeath Toll: The Halloween Drinking Game Sketch Comedy Show
Death Toll: The Halloween Drinking Game Sketch Comedy Show is listed for Chicago this weekend.
Add to calendar#17
Gene Siskel Film Center, Downtown, the Loop & West LoopFriday 5pm
Everything Else is Noise
Everything Else is Noise is listed for Chicago this weekend.
Limited Run
#17Friday 5pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#18
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville#18Friday 8:45pm · One Day Only
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville#19
Greenhouse Theater CenterOct 16, 2026–Oct 18, 2026$29
Tin Drum Theatre Company Presents the Chicago Premiere, “A Dark Wood”
Tin Drum Theatre Company Presents the Chicago Premiere, “A Dark Wood” is listed for Chicago this.
One Weekend Only
#19Oct 16, 2026–Oct 18, 2026 · One Weekend Only
Greenhouse Theater CenterTin Drum Theatre Company Presents the Chicago Premiere, “A Dark Wood”
Tin Drum Theatre Company Presents the Chicago Premiere, “A Dark Wood” is listed for Chicago this.
Add to calendar#20
City Lit Theater, Andersonville, Uptown & Lincoln SquareOct 16, 2026–Oct 18, 2026$40.00
King Hedley II
King Hedley II is listed for Chicago this weekend.
One Weekend Only
#20Oct 16, 2026–Oct 18, 2026 · One Weekend Only
City Lit Theater, Andersonville, Uptown & Lincoln Square
