#1
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
Date night in Chicago on Sunday, Halloween Weekend 2026
43 picks
The 10 best date night picks in Chicago on Sunday, Nov 1
- Dead Girl's Quinceañera — September 26 – November 1 · Owen Theatre
- Topdog/Underdog — Fri, Oct 30 7:30pm · Lincoln Park
- Theater of the Mind — Fri, Nov 13 · Tickets from $69 · Downtown
- Vladimir — Fri, Nov 13 7:30pm · Tickets $20–$60 · Lincoln Park
- Baby Wants Candy! The Original Completely Improvised Musical — Sat, Nov 14 7:30pm · $25 · Lincoln Park
- Oil Lamp Theater Presents “Dial M for Murder” — Fri, Oct 30 7:30pm · $55 · Oil Lamp Theater
- Drunk Shakespeare: Drunk Dracula (21+ Event) — Fri, Nov 6 7:00pm · Downtown
- Comedy Hour at Annoyance Theatre — Runs through Nov 13 · Free · Annoyance Theatre & Bar
- Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” — Fri, Nov 6 7:30pm · Redtwist Theatre
- I am the Wind — Fri, Oct 30 7:00pm · Theatre Y
Goodman Theatre, Owen Theatre, The Loop#1September 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#2
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 30, 2026 · 7:30pmTickets required
Topdog/Underdog
Lincoln Park, Lakeview & Wrigleyville
Topdog/Underdog at Steppenwolf Downstairs Theater.
Limited Run
#2Fri, Oct 30, 2026 · 7:30pm · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & Wrigleyville#3
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopFri, Nov 13, 2026Tickets from $69
Theater of the Mind
Downtown, the Loop & West Loop
Theater of the Mind at Reid Murdoch Building – 333 N LaSalle.
Limited Run
#3Fri, Nov 13, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#4
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleFri, Nov 13, 2026 · 7:30pmTickets $20–$60
Vladimir
Lincoln Park, Lakeview & Wrigleyville
Vladimir at Theater Wit.
Limited Run
#4Fri, Nov 13, 2026 · 7:30pm · Limited Run
Theater Wit, Lincoln Park, Lakeview & Wrigleyville#5
The Second City, Lincoln Park, Lakeview & WrigleyvilleSat, Nov 14, 2026 · 7:30pm$25
Baby Wants Candy! The Original Completely Improvised Musical
Lincoln Park, Lakeview & Wrigleyville
Baby Wants Candy! The Original Completely Improvised Musical at The Second City.
Limited Run
#5Sat, Nov 14, 2026 · 7:30pm · Limited Run
The Second City, Lincoln Park, Lakeview & WrigleyvilleBaby Wants Candy! The Original Completely Improvised Musical
Baby Wants Candy! The Original Completely Improvised Musical at The Second City.
Add to calendar#6
Oil Lamp TheaterFri, Oct 30, 2026 · 7:30pm$55
Oil Lamp Theater Presents “Dial M for Murder”
Oil Lamp Theater
Oil Lamp Theater Presents “Dial M for Murder” at Oil Lamp Theater.
Limited Run
#6Fri, Oct 30, 2026 · 7:30pm · Limited Run
Oil Lamp TheaterOil Lamp Theater Presents “Dial M for Murder”
Oil Lamp Theater Presents “Dial M for Murder” at Oil Lamp Theater.
Add to calendar#7
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopFri, Nov 6, 2026 · 7:00pm
Drunk Shakespeare: Drunk Dracula (21+ Event)
Downtown, the Loop & West Loop
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Limited Run
#7Fri, Nov 6, 2026 · 7:00pm · Limited Run
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event)
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Add to calendar#8
Annoyance Theatre & BarRuns through Nov 13, 2026Free
Comedy Hour at Annoyance Theatre
Annoyance Theatre & Bar
Comedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
FreeLimited Run
#8Runs through Nov 13, 2026 · Limited Run
Annoyance Theatre & BarComedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
Add to calendar#9
Redtwist TheatreFri, Nov 6, 2026 · 7:30pmPay what you can on Fridays
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle”
Redtwist Theatre
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” at Redtwist Theatre.
Limited Run
#9Fri, Nov 6, 2026 · 7:30pm · Limited Run
Redtwist TheatreRedtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle”
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” at Redtwist Theatre.
Add to calendar#10
Theatre Y#10Fri, Oct 30, 2026 · 7:00pm · Limited Run
Theatre YMore on Sunday
#11
The Factory TheaterFri, Nov 13, 2026 · 7:30pm$30
The Factory Theater Presents the World Premiere of “Radical Futures”
The Factory Theater
The Factory Theater Presents the World Premiere of “Radical Futures” at The Factory Theater.
Limited Run
#11Fri, Nov 13, 2026 · 7:30pm · Limited Run
The Factory TheaterThe Factory Theater Presents the World Premiere of “Radical Futures”
The Factory Theater Presents the World Premiere of “Radical Futures” at The Factory Theater.
Add to calendar#12
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln SquareSat, Nov 14, 2026 · 10:30am
Kino, Kaffee und Kuchen
Andersonville, Uptown & Lincoln Square
Kino, Kaffee und Kuchen at DANK Haus German American Cultural Center.
Limited Run
#12Sat, Nov 14, 2026 · 10:30am · Limited Run
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln SquareKino, Kaffee und Kuchen
Kino, Kaffee und Kuchen at DANK Haus German American Cultural Center.
Add to calendar#13
Redtwist TheatreFri, Nov 13, 2026 · 7:30pm$10 – $60
Redtwist Theatre’s “‘Night Mother” By Marsha Norman
Redtwist Theatre
Redtwist Theatre’s “‘Night Mother” By Marsha Norman at Redtwist Theatre.
Limited Run
#13Fri, Nov 13, 2026 · 7:30pm · Limited Run
Redtwist TheatreRedtwist Theatre’s “‘Night Mother” By Marsha Norman
Redtwist Theatre’s “‘Night Mother” By Marsha Norman at Redtwist Theatre.
Add to calendar#14
Second City-Chicago: Mainstage, 1616 N. Wells St., Lincoln Park, Lakeview & WrigleyvilleFri, Nov 13, 2026 · 6:30pm
The Second City's: Pandemonium, Please Hold
Lincoln Park, Lakeview & Wrigleyville
The Second City's: Pandemonium, Please Hold at Second City-Chicago: Mainstage.
Limited Run
#14Fri, Nov 13, 2026 · 6:30pm · Limited Run
Second City-Chicago: Mainstage, 1616 N. Wells St., Lincoln Park, Lakeview & WrigleyvilleThe Second City's: Pandemonium, Please Hold
The Second City's: Pandemonium, Please Hold at Second City-Chicago: Mainstage.
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#15
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSat, Nov 14, 2026 · 7:30pm$25
Saturday Night Sketch
Lincoln Park, Lakeview & Wrigleyville
Saturday Night Sketch at iO Theater.
Limited Run
#15Sat, Nov 14, 2026 · 7:30pm · Limited Run
iO Theater, Lincoln Park, Lakeview & Wrigleyville#16
de Maat Theatre at Second CitySat, Nov 14, 2026 · 9:30pm$20
The Improvised Movie: Summer Blockbusters
de Maat Theatre at Second City
The Improvised Movie: Summer Blockbusters at de Maat Theatre at Second City.
Limited Run
#16Sat, Nov 14, 2026 · 9:30pm · Limited Run
de Maat Theatre at Second CityThe Improvised Movie: Summer Blockbusters
The Improvised Movie: Summer Blockbusters at de Maat Theatre at Second City.
Add to calendar#17
iO Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Nov 13, 2026 · 9:30pm$15
Kohl’s Cash: Tgif (That’s Good Improv Friday)
Lincoln Park, Lakeview & Wrigleyville
Kohl’s Cash: TGIF (That’s Good Improv Friday) at iO Theater.
Limited Run
#17Fri, Nov 13, 2026 · 9:30pm · Limited Run
iO Theater, Lincoln Park, Lakeview & WrigleyvilleKohl’s Cash: Tgif (That’s Good Improv Friday)
Kohl’s Cash: TGIF (That’s Good Improv Friday) at iO Theater.
Add to calendar#18
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSun, Nov 15, 2026 · 6:00pm$15
Marquee: Musical Improv
Lincoln Park, Lakeview & Wrigleyville
Marquee: Musical Improv at iO Theater.
Limited Run
#18Sun, Nov 15, 2026 · 6:00pm · Limited Run
iO Theater, Lincoln Park, Lakeview & Wrigleyville#19
The Annoyance TheatreFri, Nov 13, 2026 · 8:00pm$15
Missed Call Sketch Comedy Show
The Annoyance Theatre
Missed Call Sketch Comedy Show at The Annoyance Theatre.
Limited Run
#19Fri, Nov 13, 2026 · 8:00pm · Limited Run
The Annoyance TheatreMissed Call Sketch Comedy Show
Missed Call Sketch Comedy Show at The Annoyance Theatre.
Add to calendar#20
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USAFri, Nov 13, 2026 · 10:00pm$15
Voila: The Improvised Musical
IL 60642, USA
Voila: The Improvised Musical at The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,.
Limited Run
#20Fri, Nov 13, 2026 · 10:00pm · Limited Run
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USAVoila: The Improvised Musical
Voila: The Improvised Musical at The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USA,.
Add to calendar#21
Peppa Pig World of Play ChicagoFri, Nov 13, 2026 · 10:00am
Homeschool Days at Peppa PIG World of Play Chicago
Peppa Pig World of Play Chicago
Homeschool Days at PEPPA PIG World of Play Chicago at Peppa Pig World of Play Chicago.
Limited Run
#21Fri, Nov 13, 2026 · 10:00am · Limited Run
Peppa Pig World of Play ChicagoHomeschool Days at Peppa PIG World of Play Chicago
Homeschool Days at PEPPA PIG World of Play Chicago at Peppa Pig World of Play Chicago.
Add to calendar#22
Lifeline TheatreSat, Nov 7, 2026 · 11:00am$22
Sugar Plum Fairy, P.I.
Lifeline Theatre
Sugar Plum Fairy, P.I. at Lifeline Theatre.
Limited Run
#22Sat, Nov 7, 2026 · 11:00am · Limited Run
Lifeline Theatre#23
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleFri, Nov 13, 2026 · 7:30pm$28 – $37
Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear”
Lincoln Park, Lakeview & Wrigleyville
Babes With Blades Theatre Company Presents William Shakespeare’s “King Lear” at Theater Wit.
Limited Run
#23Fri, Nov 13, 2026 · 7:30pm · Limited Run
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” at Theater Wit.
Add to calendar#24
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West LoopSat, Nov 7, 2026 · 7:00pm
The Winter's Tale
Downtown, the Loop & West Loop
The Winter's Tale at Chicago Shakespeare Theater.
Limited Run
#24Sat, Nov 7, 2026 · 7:00pm · Limited Run
Chicago Shakespeare Theater, 800 East Grand Avenue on Navy Pier, Downtown, the Loop & West LoopAbout this list
Stumblday's hand-checked ranking of the best date night in Chicago on Sunday of Halloween weekend, Nov 1: 43 picks, refreshed weekly.
