#1
Gene Siskel Film Center, Downtown, the Loop & West LoopWednesday · Oct 14
THE VANISHING
Downtown, the Loop & West Loop
Screening at Gene Siskel Film Center October 14 at. Listed on Gene Siskel Film Center's official calendar.
FilmLimited Run
Date night in Chicago on Wednesday, Oct 14
17 picks
The 10 best date night in Chicago on Wednesday, Oct 14
- THE VANISHING — Wednesday Oct 14 · Downtown
- CHRONO TRIGGER Orchestra Concert: Melodies Across Time — Wednesday Oct 14 · Downtown
- Hack Job — Wednesday Oct 14 · $10 · Blind Barber
- DESTROY ALL MONSTERS — Wednesday Oct 14 · Downtown
- Crowd Work Wednesday — Wednesday Oct 14 · $22 – $25 · Downtown
- Come From Away — Wednesday Oct 14 · $80 – $100 · Marriott Theatre
- Dial M for Murder — Wednesday Oct 14 · $55 · Oil Lamp Theater
- Escape to Margaritaville — Wednesday Oct 14 · 9501 Skokie Blvd
- Play Time — Wednesday Oct 14 · $18 · Lincoln Park
- Respawn Improv with Blue.0 — Wednesday Oct 14 · $13 · Lincoln Park
Gene Siskel Film Center, Downtown, the Loop & West Loop#1Wednesday · Oct 14 · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopTHE VANISHING
Screening at Gene Siskel Film Center October 14 at. Listed on Gene Siskel Film Center's official calendar.
Add to calendar#2
Auditorium Theatre, Downtown, the Loop & West LoopWednesday · Oct 14
CHRONO TRIGGER Orchestra Concert: Melodies Across Time
Downtown, the Loop & West Loop
Performance at Auditorium Theatre October 14 at 8 PM. Listed on Auditorium Theatre's official calendar.
TheaterLimited Run
#2Wednesday · Oct 14 · Limited Run
Auditorium Theatre, Downtown, the Loop & West LoopCHRONO TRIGGER Orchestra Concert: Melodies Across Time
Performance at Auditorium Theatre October 14 at 8 PM. Listed on Auditorium Theatre's official calendar.
Add to calendar#3
Blind BarberWednesday · Oct 14$10
Hack Job
Blind Barber
Maureen Nolan and Lizz Evalen host a $10 Chicago comedy showcase in Fulton Market.
10ComedyFulton Market
#3Wednesday · Oct 14 · One Day Only
Blind BarberHack Job
Maureen Nolan and Lizz Evalen host a $10 Chicago comedy showcase in Fulton Market.
Add to calendar#4
Gene Siskel Film Center, Downtown, the Loop & West LoopWednesday · Oct 14
DESTROY ALL MONSTERS
Downtown, the Loop & West Loop
Screening at Gene Siskel Film Center October 14 at 6 PM. Listed on Gene Siskel Film Center's official calendar.
FilmLimited Run
#4Wednesday · Oct 14 · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopDESTROY ALL MONSTERS
Screening at Gene Siskel Film Center October 14 at 6 PM. Listed on Gene Siskel Film Center's official calendar.
Add to calendar#5
The Comedy Bar, Downtown, the Loop & West LoopWednesday · Oct 14$22 – $25
Crowd Work Wednesday
Downtown, the Loop & West Loop
Pat Bolduc and John Gasper host rotating comics in an audience-powered crowd-work show.
ComedyCrowd WorkInteractive
#5Wednesday · Oct 14 · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopCrowd Work Wednesday
Pat Bolduc and John Gasper host rotating comics in an audience-powered crowd-work show.
Add to calendar#6
Marriott TheatreWednesday · Oct 14$80 – $100
Come From Away
Marriott Theatre
Marriott Theatre stages the award-recognized ensemble musical Come From Away in a 1 PM matinee.
MusicalMatineeSuburbs
#6Wednesday · Oct 14 · One Day Only
Marriott TheatreCome From Away
Marriott Theatre stages the award-recognized ensemble musical Come From Away in a 1 PM matinee.
Add to calendar#7
Oil Lamp TheaterWednesday · Oct 14$55
Dial M for Murder
Oil Lamp Theater
Oil Lamp Theater stages Jeffrey Hatcher's modern adaptation of the classic murder thriller.
ThrillerTheaterGlenview
#7Wednesday · Oct 14 · One Day Only
Oil Lamp TheaterDial M for Murder
Oil Lamp Theater stages Jeffrey Hatcher's modern adaptation of the classic murder thriller.
Add to calendar#8
North Theatre at North Shore Center for the Performing Arts, 9501 Skokie Blvd, Evanston & Oak ParkWednesday · Oct 14
Escape to Margaritaville
9501 Skokie Blvd, Evanston & Oak Park
Music Theater Works presents Escape to Margaritaville in a Wednesday matinee in Skokie.
MusicalMatineeSkokie
#8Wednesday · Oct 14 · Limited Run
North Theatre at North Shore Center for the Performing Arts, 9501 Skokie Blvd, Evanston & Oak ParkEscape to Margaritaville
Music Theater Works presents Escape to Margaritaville in a Wednesday matinee in Skokie.
Add to calendar#9
iO Theater, Lincoln Park, Lakeview & WrigleyvilleWednesday · Oct 14$18
Play Time
Lincoln Park, Lakeview & Wrigleyville
iO performers stage three experimental short plays developed by selected writing teams.
Short PlaysExperimentaliO Theater
#9Wednesday · Oct 14 · One Day Only
iO Theater, Lincoln Park, Lakeview & WrigleyvillePlay Time
iO performers stage three experimental short plays developed by selected writing teams.
Add to calendar#10
iO Theater, Lincoln Park, Lakeview & WrigleyvilleWednesday · Oct 14$13
Respawn Improv with Blue.0
Lincoln Park, Lakeview & Wrigleyville
Blue.0 hosts indie improv teams and invites selected audience members into the performance.
ImprovInteractive13
#10Wednesday · Oct 14 · One Day Only
iO Theater, Lincoln Park, Lakeview & WrigleyvilleRespawn Improv with Blue.0
Blue.0 hosts indie improv teams and invites selected audience members into the performance.
Add to calendarAlso open Wed, Oct 14 — check hours
#11
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
Downtown, the Loop & West Loop
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Limited Run
#11September 11–October 18, 2026; selected performances · Limited Run
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopPlay On! — Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Add to calendar#12
Music Box Theatre, LakeviewOctober 1–31, 2026; horror screenings most nights, plus a 24-hour marathon on October 24Most screenings $13 ($10 Musi…
Music Box of Horrors: The Final Chapter
Music Box Theatre, Lakeview
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
Limited Run
#12October 1–31, 2026; horror screenings most nights, plus a 24-hour marathon on October 24 · Limited Run
Music Box Theatre, LakeviewMusic Box of Horrors: The Final Chapter
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
Add to calendar#13
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareOctober 8 – November 8, 2026Tickets via Raven Theatre
A Strange Loop
Andersonville, Uptown & Lincoln Square
A Strange Loop is listed for Chicago this weekend.
Limited Run
#13October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#14
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsSeptember 15 – October 25, 2026Ticketed via Lookingglass The…
Kowalski
Downtown, the Loop & West Loop
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Limited Run
#14September 15 – October 25, 2026 · Limited Run
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsKowalski
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Add to calendarThe whole weekend, in one email.
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#15
Stolp Island Theatre, Aurora, Far SuburbsOctober 7, 2026 – January 3, 2027$87 in person
Million Dollar Quartet
Aurora, Far Suburbs
Million Dollar Quartet is listed for Chicago this weekend.
Limited Run
#15October 7, 2026 – January 3, 2027 · Limited Run
Stolp Island Theatre, Aurora, Far Suburbs#16
Goodman Theatre, Owen Theatre, The LoopSeptember 26 – November 1, 2026Tickets via the Goodman
Dead Girl's Quinceañera
Owen Theatre, The Loop
Three friends investigate a classmate’s quinceañera disappearance in this comic thriller.
Limited Run
#16September 26 – November 1, 2026 · Limited Run
Goodman Theatre, Owen Theatre, The LoopDead Girl's Quinceañera
Three friends investigate a classmate’s quinceañera disappearance in this comic thriller.
Add to calendar#17
Northlight Theatre, EvanstonSeptember 9 – October 25, 2026 (extended)Ticketed
The Front Page
Northlight Theatre, Evanston
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Limited Run
#17September 9 – October 25, 2026 (extended) · Limited Run
Northlight Theatre, EvanstonThe Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Add to calendarAbout this list
Stumblday's ranked list of the best things to do in Chicago on Wednesday, October 14: 24 events, led by The Bolero Project, The Smashing Pumpkins: The Rats In A Cage Tour and THE VANISHING — each one checked against the organizer's own page. Below them, 24 exhibitions and shows running through the day.