#1
Friday, October 2, 2026, 7:30 PM; Saturday, October 3, 7:00 PM and 10:00 PM
Bill Burr Live
Bill Burr, host of the Monday Morning Podcast and creator of specials including Paper Tiger, takes his stand-up to the Chicago Theatre.
One Weekend Only
Date night in Chicago the Weekend of Oct 2–4, 2026
Stumblday's hand-checked ranking of the best date night in Chicago the weekend of Oct 2–4, 2026: 90 picks, refreshed weekly.
90 picks · checked Sep 21
90 picks
#1Friday, October 2, 2026, 7:30 PM; Saturday, October 3, 7:00 PM and 10:00 PM · One Weekend Only
Bill Burr Live
Bill Burr, host of the Monday Morning Podcast and creator of specials including Paper Tiger, takes his stand-up to the Chicago Theatre.
Add to calendar#2
Downstairs Theatre At Steppenwolf Theatre – Chicago, Lincoln Park, Lakeview & Wrigleyvillevictorgrigas · CC BY-SA 3.0 · Wikimedia CommonsFriday, October 2, 7:30 p.m.; Saturday, October 3, 3 and 7:30 p.m.; Sunday, October 4, 3 p.m.$50 – $171
Topdog/Underdog – Chicago
A play about brotherhood, identity and survival in Steppenwolf's intimate Downstairs Theatre.
One Weekend Only
#2Friday, October 2, 7:30 p.m.; Saturday, October 3, 3 and 7:30 p.m.; Sunday, October 4, 3 p.m. · One Weekend Only
Downstairs Theatre At Steppenwolf Theatre – Chicago, Lincoln Park, Lakeview & Wrigleyvillevictorgrigas · CC BY-SA 3.0 · Wikimedia CommonsTopdog/Underdog – Chicago
A play about brotherhood, identity and survival in Steppenwolf's intimate Downstairs Theatre.
Add to calendar#3
CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopFriday, October 2, 7 p.m.; Saturday, October 3, 2 and 7:30 p.m.; Sunday, October 4, 1 and 6:30 p.m.
Operation Mincemeat (Chicago)
Operation Mincemeat turns a bizarre Second World War deception plot into a musical comedy at the CIBC Theatre.
One Weekend Only
#3Friday, October 2, 7 p.m.; Saturday, October 3, 2 and 7:30 p.m.; Sunday, October 4, 1 and 6:30 p.m. · One Weekend Only
CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopOperation Mincemeat (Chicago)
Operation Mincemeat turns a bizarre Second World War deception plot into a musical comedy at the CIBC Theatre.
Add to calendar#4
The Den Theatre, Logan Square, Wicker Park & BucktownFinal weekend: through Oct 3, 2026$35.00
Blood of the Lamb
A drama about a pregnant woman held in a room after her flight is diverted to Dallas.
Limited Run
#4Final weekend: through Oct 3, 2026 · Limited Run
The Den Theatre, Logan Square, Wicker Park & BucktownBlood of the Lamb
A drama about a pregnant woman held in a room after her flight is diverted to Dallas.
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#5
American Blues Theater, Andersonville, Uptown & Lincoln SquareFinal weekend: through Oct 4, 2026
Black Girl From a White Suburb
Tania Richard's solo show adapts her memoir of growing up in an all-white Chicago suburb.
Limited Run
#5Final weekend: through Oct 4, 2026 · Limited Run
American Blues Theater, Andersonville, Uptown & Lincoln SquareBlack Girl From a White Suburb
Tania Richard's solo show adapts her memoir of growing up in an all-white Chicago suburb.
Add to calendar#6
Victory Gardens Theater, Lincoln Park, Lakeview & WrigleyvilleMarc Heiden - User: (WT-shared) Gorilla Jones at wts wikivoyage · CC BY-SA 3.0 · Wikimedia CommonsThrough October 4, 2026; Thursdays and Fridays at 7:30pm, Saturdays at 2:30 and 7:30pm, Sundays at 3pmTickets from $25 via Eventbri…
The Humanities (World Premiere)
A world premiere that drops a campus speaker into a faculty at war,.
Limited Run
#6Through October 4, 2026; Thursdays and Fridays at 7:30pm, Saturdays at 2:30 and 7:30pm, Sundays at 3pm · Limited Run
Victory Gardens Theater, Lincoln Park, Lakeview & WrigleyvilleMarc Heiden - User: (WT-shared) Gorilla Jones at wts wikivoyage · CC BY-SA 3.0 · Wikimedia CommonsThe Humanities (World Premiere)
A world premiere that drops a campus speaker into a faculty at war,.
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A Red Orchid Theatre, Old Town, Lincoln Park, Lakeview & WrigleyvilleJim Hudgins/USFWS. Illustrative bird image. · public domain · Wikimedia CommonsSeptember 10–October 4, 2026; performance times vary$55 general admission
Birds of North America
Catch the four-Jeff-Award return engagement before its limited run closes Sunday.
Limited Run
#7September 10–October 4, 2026; performance times vary · Limited Run
A Red Orchid Theatre, Old Town, Lincoln Park, Lakeview & WrigleyvilleJim Hudgins/USFWS. Illustrative bird image. · public domain · Wikimedia CommonsBirds of North America
Catch the four-Jeff-Award return engagement before its limited run closes Sunday.
Add to calendar#8
City Lit Theater, Andersonville, Uptown & Lincoln SquareFinal weekend: through Oct 4, 2026$40.00
Shane
City Lit Theater premieres a stage adaptation of the classic western Shane.
Limited Run
#8Final weekend: through Oct 4, 2026 · Limited Run
City Lit Theater, Andersonville, Uptown & Lincoln Square#9
Goodman Albert Theatre, Downtown, the Loop & West LoopMichel Curi · CC BY 2.0 · Wikimedia CommonsThrough Oct 4, 2026
The Attic
The 7 Fingers turn a former trapezist's memoir into daring aerial theater, running into October.
Limited Run
#9Through Oct 4, 2026 · Limited Run
Goodman Albert Theatre, Downtown, the Loop & West LoopMichel Curi · CC BY 2.0 · Wikimedia CommonsThe Attic
The 7 Fingers turn a former trapezist's memoir into daring aerial theater, running into October.
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Landmark Century Centre Cinema, Lakeview, Lincoln Park, Lakeview & WrigleyvilleDiscoA340 · CC0 · Wikimedia CommonsFriday, October 2, 7–11 p.m.; Saturday, October 3, 11 a.m.–midnight; Sunday, October 4, 11 a.m.–10 p.m.$15.56–$70.26
28th Annual Chicago Horror Film Festival
Catch three days of indie horror screenings, filmmaker meetups and a late-night queer block.
One Weekend Only
#10Friday, October 2, 7–11 p.m.; Saturday, October 3, 11 a.m.–midnight; Sunday, October 4, 11 a.m.–10 p.m. · One Weekend Only
Landmark Century Centre Cinema, Lakeview, Lincoln Park, Lakeview & WrigleyvilleDiscoA340 · CC0 · Wikimedia Commons28th Annual Chicago Horror Film Festival
Catch three days of indie horror screenings, filmmaker meetups and a late-night queer block.
Add to calendar#11
Friday, October 2, 7 and 9:15 p.m.; Saturday, October 3, 7 and 9:15 p.m.
Ali Macofsky
Ali Macofsky headlines four Zanies sets across Friday and Saturday night.
One Weekend Only
#11Friday, October 2, 7 and 9:15 p.m.; Saturday, October 3, 7 and 9:15 p.m. · One Weekend Only
Ali Macofsky
Ali Macofsky headlines four Zanies sets across Friday and Saturday night.
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The Vic Theatre, Lincoln Park, Lakeview & WrigleyvillePaul R. Burley · CC0 · Wikimedia CommonsSun, Oct 4, 2026 · 7:30pm
Watch What Crappens – Chicago, IL – In The Mix Tour
The Bravo recap podcast brings its award-winning mix of gossip and comedy to the Vic.
One Day Only
#12Sun, Oct 4, 2026 · 7:30pm · One Day Only
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvillePaul R. Burley · CC0 · Wikimedia CommonsWatch What Crappens – Chicago, IL – In The Mix Tour
The Bravo recap podcast brings its award-winning mix of gossip and comedy to the Vic.
Add to calendar#13
Sat, Oct 3, 2026 · 8:00pm
Cristian Castro – Nada Solo Exitos Tour
Cristian Castro plays his Nada Solo Exitos Tour at Rosemont Theatre.
Limited Run
#13Sat, Oct 3, 2026 · 8:00pm · Limited Run
Cristian Castro – Nada Solo Exitos Tour
Cristian Castro plays his Nada Solo Exitos Tour at Rosemont Theatre.
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Theater Wit, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 2, 2026 · 7:30pm$20–$60
Vladimir
Erika Sheffer's Vladimir follows an independent journalist under a new Russian regime.
One Weekend Only
#14Fri, Oct 2, 2026 · 7:30pm · One Weekend Only
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleVladimir
Erika Sheffer's Vladimir follows an independent journalist under a new Russian regime.
Add to calendar#15
The Lincoln Lodge, Logan Square, Wicker Park & BucktownThursday–Saturday, October 1–3, 2026; 18 shows, with Friday and Saturday sessions in the target weekend$20
The 5th Annual Latina Comedy Festival
Eighteen showcases bring Latina comedians to the Lincoln Lodge across three nights.
One Weekend Only
#15Thursday–Saturday, October 1–3, 2026; 18 shows, with Friday and Saturday sessions in the target weekend · One Weekend Only
The Lincoln Lodge, Logan Square, Wicker Park & BucktownThe 5th Annual Latina Comedy Festival
Eighteen showcases bring Latina comedians to the Lincoln Lodge across three nights.
Add to calendar#16
Cermak Hall at Radius, Pilsen, West Town & the West SideFriday, October 2, 2026; doors 10 p.m., ending 3:30 a.m. SaturdayTicketed
Indo Warehouse with Anyasa and Harji
Indo Warehouse blends South Asian rhythms with house and techno inside Cermak Hall.
One Day Only
#16Friday, October 2, 2026; doors 10 p.m., ending 3:30 a.m. Saturday · One Day Only
Cermak Hall at Radius, Pilsen, West Town & the West SideIndo Warehouse with Anyasa and Harji
Indo Warehouse blends South Asian rhythms with house and techno inside Cermak Hall.
Add to calendar#17
Columbia College Chicago Dance Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsFri, Oct 2, 2026 · 7:30pm$35
Cerqua Rivera Dance Theatre Presents the Second Chicago Latinx/e Contemporary Movement Festival at the Dance Center of Columbia College
Cerqua Rivera hosts a Latinx/e contemporary movement festival at the Dance Center for $35.
One Day Only
#17Fri, Oct 2, 2026 · 7:30pm · One Day Only
Columbia College Chicago Dance Center, Downtown, the Loop & West LoopBeyond My Ken · CC BY-SA 4.0 · Wikimedia CommonsCerqua Rivera Dance Theatre Presents the Second Chicago Latinx/e Contemporary Movement Festival at the Dance Center of Columbia College
Cerqua Rivera hosts a Latinx/e contemporary movement festival at the Dance Center for $35.
Add to calendar#18
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
#18Open 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.
#19
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
Duke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
Limited Run
#19September 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
Duke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
Add to calendar#20
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loopw_lemay · CC BY-SA 2.0 · Wikimedia CommonsThrough November 8, 2026
Jekyll & Hyde
Kokandy's 10-time Jeff-nominated musical revival, back after a sold-out, extended Chicago run.
Limited Run
#20Through November 8, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loopw_lemay · CC BY-SA 2.0 · Wikimedia CommonsJekyll & Hyde
Kokandy's 10-time Jeff-nominated musical revival, back after a sold-out, extended Chicago run.
Add to calendar#21
Fri, Oct 2, 2026 · 7:00pm
World Ballet Company: Swan Lake
World Ballet Company brings Swan Lake’s transformations and Tchaikovsky score to Skokie with a cast of 50.
Limited Run
#21Fri, Oct 2, 2026 · 7:00pm · Limited Run
World Ballet Company: Swan Lake
World Ballet Company brings Swan Lake’s transformations and Tchaikovsky score to Skokie with a cast of 50.
Add to calendar#22
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsSunday 4:15pm
ACE IN THE Hole
Catch this film screening at the Gene Siskel Film Center afternoon.
Limited Run
#22Sunday 4:15pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia Commons#23
The Den Theatre, Wicker Park, Logan Square, Wicker Park & BucktownFriday–Saturday, October 2–3, 2026, 7:15 and 9:30 p.m. nightlyFrom $28
Noel Miller: Special Taping
Miller films four stand-up sets over two nights on The Den’s intimate Heath Mainstage.
One Weekend Only
#23Friday–Saturday, October 2–3, 2026, 7:15 and 9:30 p.m. nightly · One Weekend Only
The Den Theatre, Wicker Park, Logan Square, Wicker Park & BucktownNoel Miller: Special Taping
Miller films four stand-up sets over two nights on The Den’s intimate Heath Mainstage.
Add to calendar#24
The Second City, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 2, 2026 · 8:00pm
Best of The Second City
Second City revisits sketches and songs from its archive, updated alongside newer material.
One Weekend Only
#24Fri, Oct 2, 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.
Add to calendar