#1
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 7:30pm
Topdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Limited Run
Date night in Chicago on Columbus Day Monday, Oct 12
Stumblday's hand-checked ranking of the best date night in Chicago on Columbus Day Monday, Oct 12: 24 picks, refreshed weekly.
24 picks · checked Sep 21
24 picks
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & Wrigleyville#1Fri, Oct 9, 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
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Limited Run
#2September 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#3
Historic Main Stage at Athenaeum Center, Lincoln Park, Lakeview & WrigleyvilleKeiko Oikawa · Public domain · Wikimedia CommonsMon, Oct 12, 2026 · 7:30pm
Simple TOO Live: An Evening with Yotam Ottolenghi
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
One Day Only
#3Mon, Oct 12, 2026 · 7:30pm · One Day Only
Historic Main Stage at Athenaeum Center, Lincoln Park, Lakeview & WrigleyvilleKeiko Oikawa · Public domain · Wikimedia CommonsSimple TOO Live: An Evening with Yotam Ottolenghi
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
Add to calendar#4
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM$20 individual programs
Cinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
One Weekend Only
#4Sunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM · One Weekend Only
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleCinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
Add to calendarPlanning ahead for Oct 9–12, 2026?
It lands the Friday before, plus every Friday until then. Unsubscribe anytime.
#5
Green Mill Cocktail Lounge, Uptown, Andersonville, Uptown & Lincoln SquareKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsSaturdays at 3pm (doors 1pm); no end date announcedFREE
The Paper Machete
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
FreeLimited Run
#5Saturdays at 3pm (doors 1pm); no end date announced · Limited Run
Green Mill Cocktail Lounge, Uptown, Andersonville, Uptown & Lincoln SquareKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsThe Paper Machete
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
Add to calendar#6
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleMonday, October 12, 2026 · 7 PM; post-film director Q&A$15 general admission
Begotten: New Restoration with E. Elias Merhige
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Limited Run
#6Monday, October 12, 2026 · 7 PM; post-film director Q&A · Limited Run
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleBegotten: New Restoration with E. Elias Merhige
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Add to calendar#7
Northlight Theatre, Evanston, Evanston & Oak ParkSeptember 9 – October 25, 2026 (extended)Ticketed
The Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Limited Run
#7September 9 – October 25, 2026 (extended) · Limited Run
Northlight Theatre, Evanston, Evanston & Oak ParkThe Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Add to calendar#8
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsAugust 19–October 18, 2026Tickets via Drury Lane box of…
The Buddy Holly Story
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Limited Run
#8August 19–October 18, 2026 · Limited Run
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsThe Buddy Holly Story
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Add to calendar#9
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareOctober 8 – November 8, 2026Tickets via Raven Theatre
A Strange Loop
A Strange Loop has enough weekend energy to earn a spot on the board.
Limited Run
#9October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#10
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsMonday 7pm
Faust with Live Score by ten thousand lakes
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
Limited Run
#10Monday 7pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsFaust with Live Score by ten thousand lakes
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
Add to calendar#11
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopExtended through November 15, 2026; 75-minute timed performances
Theater of the Mind
Theater of the Mind has enough weekend energy to earn a spot on the board.
Limited Run
#11Extended through November 15, 2026; 75-minute timed performances · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopTheater of the Mind
Theater of the Mind has enough weekend energy to earn a spot on the board.
Add to calendar#12
Theatre Y, Pilsen, West Town & the West SideSeptember 24–November 1, 2026; Thu–Sat 7 p.m., Sun 5 p.m.FREE
I am the Wind
Theatre Y stages Nobel laureate Jon Fosse's two-hander I Am the Wind.
Limited Run
#12September 24–November 1, 2026; Thu–Sat 7 p.m., Sun 5 p.m. · Limited Run
Theatre Y, Pilsen, West Town & the West Side#13
Facility Theatre, Logan Square, Wicker Park & BucktownSeptember 20–October 26, 2026; times and venues varyPay what you can
37th Annual Rhinoceros Theater Festival
37th Annual Rhinoceros Theater Festival has enough weekend energy to earn a spot on the board.
Limited Run
#13September 20–October 26, 2026; times and venues vary · Limited Run
Facility Theatre, Logan Square, Wicker Park & Bucktown37th Annual Rhinoceros Theater Festival
37th Annual Rhinoceros Theater Festival has enough weekend energy to earn a spot on the board.
Add to calendar#14
The Space at Rockwell, Lincoln Park, Lakeview & WrigleyvilleOctober 9–25, 2026$45
T A K E
T A K E has enough weekend energy to earn a spot on the board.
Limited Run
#14October 9–25, 2026 · Limited Run
The Space at Rockwell, Lincoln Park, Lakeview & Wrigleyville#15
The Second City, Lincoln Park, Lakeview & WrigleyvilleOpen run
Best of the Second City
A greatest-hits revue from the comedy theater that launched Tina Fey and Steve Carell.
Limited Run
#15Open run · Limited Run
The Second City, Lincoln Park, Lakeview & WrigleyvilleBest of the Second City
A greatest-hits revue from the comedy theater that launched Tina Fey and Steve Carell.
Add to calendar#16
iO Theater, Lincoln Park, Lakeview & WrigleyvilleMon, Oct 12, 2026 · 7:00pm$17
The Armando Diaz
The Armando Diaz has enough weekend energy to earn a spot on the board.
One Day Only
#16Mon, Oct 12, 2026 · 7:00pm · One Day Only
iO Theater, Lincoln Park, Lakeview & WrigleyvilleThe Armando Diaz
The Armando Diaz has enough weekend energy to earn a spot on the board.
Add to calendar#17
The Comedy Bar, Downtown, the Loop & West LoopMon, Oct 12, 2026 · 7:00pm$25 – $30
Late Nite Mic w/ Vik Pandya at The Comedy Bar
Late Nite Mic w/ Vik Pandya at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Day Only
#17Mon, Oct 12, 2026 · 7:00pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopLate Nite Mic w/ Vik Pandya at The Comedy Bar
Late Nite Mic w/ Vik Pandya at The Comedy Bar has enough weekend energy to earn a spot on the board.
Add to calendar#18
Apollo Theater, Lincoln Park, Lakeview & WrigleyvilleAugust 20, 2026–January 3, 2027$45
Vape! The Grease Parody
Vape! The Grease Parody has enough weekend energy to earn a spot on the board.
Limited Run
#18August 20, 2026–January 3, 2027 · Limited Run
Apollo Theater, Lincoln Park, Lakeview & WrigleyvilleVape! The Grease Parody
Vape! The Grease Parody has enough weekend energy to earn a spot on the board.
Add to calendar#19
iO Theater, Lincoln Park, Lakeview & WrigleyvilleMon, Oct 12, 2026 · 9:00pm$10
$10 Improv Night
$10 Improv Night has enough weekend energy to earn a spot on the board.
One Day Only
#19Mon, Oct 12, 2026 · 9:00pm · One Day Only
iO Theater, Lincoln Park, Lakeview & Wrigleyville$10 Improv Night
$10 Improv Night has enough weekend energy to earn a spot on the board.
Add to calendar#20
Stolp Island Theatre, Aurora, Far SuburbsOctober 7, 2026 – January 3, 2027$87 in person
Million Dollar Quartet
Million Dollar Quartet has enough weekend energy to earn a spot on the board.
Limited Run
#20October 7, 2026 – January 3, 2027 · Limited Run
Stolp Island Theatre, Aurora, Far SuburbsMillion Dollar Quartet
Million Dollar Quartet has enough weekend energy to earn a spot on the board.
Add to calendar#21
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopSeptember 26 – November 1, 2026Tickets via the Goodman
Dead Girl's Quinceañera
Dead Girl's Quinceañera has enough weekend energy to earn a spot on the board.
Limited Run
#21September 26 – November 1, 2026 · Limited Run
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopDead Girl's Quinceañera
Dead Girl's Quinceañera has enough weekend energy to earn a spot on the board.
Add to calendar#22
Black Ensemble Theater, Uptown, Andersonville, Uptown & Lincoln SquareSep 5 – Oct 25, 2026Ticketed via Black Ensemble T…
You Can't Fake the Funk
You Can't Fake the Funk has enough weekend energy to earn a spot on the board.
Limited Run
#22Sep 5 – Oct 25, 2026 · Limited Run
Black Ensemble Theater, Uptown, Andersonville, Uptown & Lincoln SquareYou Can't Fake the Funk
You Can't Fake the Funk has enough weekend energy to earn a spot on the board.
Add to calendar#23
Writers Theatre, Glencoe, Far SuburbsAugust 13–November 8, 2026Ticketed
Sisters at Writers Theatre
Sisters at Writers Theatre has enough weekend energy to earn a spot on the board.
Limited Run
#23August 13–November 8, 2026 · Limited Run
Writers Theatre, Glencoe, Far SuburbsSisters at Writers Theatre
Sisters at Writers Theatre has enough weekend energy to earn a spot on the board.
Add to calendar#24
Redtwist TheatreSeptember 17 – November 8, 2026; previews Sep 17–19, opens Sun, Sep 20$50
Prayer Circle
Redtwist opens its 22nd season with Erik Gernand's Prayer Circle.
Limited Run
#24September 17 – November 8, 2026; previews Sep 17–19, opens Sun, Sep 20 · Limited Run
Redtwist Theatre