#1
Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pmTicket required
Jerry Seinfeld Live!
Downtown, the Loop & West Loop
The stand-up legend does a live set at the Chicago Theatre, one night only.
One Weekend Only
Date night in Chicago Columbus Day Weekend 2026
81 picks
The 10 best date night picks in Chicago over Columbus Day Weekend (Oct 9–12)
- Jerry Seinfeld Live! — Fri, Oct 9 7pm; Sat, Oct 10 · 5pm and 8pm · Downtown
- Lincoln Park Wine Fest — October 9–11; Friday 5–10pm · General admission from $30 · Lincoln Park
- Operation Mincemeat: A New Musical — Through Oct 11 · Downtown
- Topdog/Underdog — Runs September 18–October 18 · Lincoln Park
- Jekyll& Hyde — Oct 2–Oct 18, 2026 · Downtown
- Music Box of Horrors: Possession, In the Mouth of Madness & Event Horizon — Saturday, October 10, 6:45 PM · $13 for most screenings · Lakeview
- Mean Girls — Through Oct 11 · From $34 in person · Aurora
- Idle Muse Theatre Company Presents “Witch” — Runs through Saturday, October 10. · $20–$30 · Andersonville
- Drunk Shakespeare: Drunk Dracula (21+ Event) — Runs through Oct 9 · Downtown
- Play On! — Chicago Shakespeare Theater — September 11–October 18; selected performances · Downtown
#1Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pm · One Weekend Only
Jerry Seinfeld Live!
The stand-up legend does a live set at the Chicago Theatre, one night only.
Add to calendar#2
Jonquil Park, Lincoln ParkWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsOctober 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pmGeneral admission from $30
Lincoln Park Wine Fest
Jonquil Park, Lincoln Park
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
One Weekend Only
#2October 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pm · One Weekend Only
Jonquil Park, Lincoln ParkWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsLincoln Park Wine Fest
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
Add to calendar#3
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsThrough Oct 11, 2026
Operation Mincemeat: A New Musical
Downtown, the Loop & West Loop
The Olivier-winning musical about a WWII deception plot built around a dead body.
One Weekend Only
#3Through Oct 11, 2026 · One Weekend Only
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsOperation Mincemeat: A New Musical
The Olivier-winning musical about a WWII deception plot built around a dead body.
Add to calendar#4
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleRuns September 18–October 18, 2026; weekend performances.
Topdog/Underdog
Lincoln Park, Lakeview & Wrigleyville
Topdog/Underdog brings its two-brother drama to Steppenwolf’s Downstairs Theater.
Limited Run
#4Runs September 18–October 18, 2026; weekend performances. · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog
Topdog/Underdog brings its two-brother drama to Steppenwolf’s Downstairs Theater.
Add to calendar#5
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West LoopOct 2, 2026–Oct 18, 2026
Jekyll& Hyde
Downtown, the Loop & West Loop
Jekyll& Hyde is listed for Chicago this weekend.
Limited Run
#5Oct 2, 2026–Oct 18, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#6
Music Box Theatre, LakeviewBrandon Olafsson · CC BY 2.0 · Wikimedia CommonsSaturday, October 10, 2026, 6:45 PM$13 for most screenings
Music Box of Horrors: Possession, In the Mouth of Madness & Event Horizon
Music Box Theatre, Lakeview
Music Box of Horrors lines up three supernatural films at the Music Box Theatre.
One Day Only
#6Saturday, October 10, 2026, 6:45 PM · One Day Only
Music Box Theatre, LakeviewBrandon Olafsson · CC BY 2.0 · Wikimedia CommonsMusic Box of Horrors: Possession, In the Mouth of Madness & Event Horizon
Music Box of Horrors lines up three supernatural films at the Music Box Theatre.
Add to calendar#7
Paramount Theatre, Aurora, Far SuburbsJoseph Gage · CC BY-SA 2.0 · Wikimedia CommonsThrough Oct 11, 2026From $34 in person
Mean Girls
Aurora, Far Suburbs
The Chicago-area premiere of the Tina Fey musical, a big Equity production in Aurora from $34.
Limited Run
#7Through Oct 11, 2026 · Limited Run
Paramount Theatre, Aurora, Far SuburbsJoseph Gage · CC BY-SA 2.0 · Wikimedia CommonsMean Girls
The Chicago-area premiere of the Tina Fey musical, a big Equity production in Aurora from $34.
Add to calendar#8
The Edge Off Broadway Theatre, Andersonville, Uptown & Lincoln SquareRuns through Saturday, October 10, 2026.$20–$30
Idle Muse Theatre Company Presents “Witch”
Andersonville, Uptown & Lincoln Square
Idle Muse Theatre Company stages Jen Silverman's Witch for its 20th season.
Limited Run
#8Runs through Saturday, October 10, 2026. · Limited Run
The Edge Off Broadway Theatre, Andersonville, Uptown & Lincoln SquareIdle Muse Theatre Company Presents “Witch”
Idle Muse Theatre Company stages Jen Silverman's Witch for its 20th season.
Add to calendar#9
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopRuns through Oct 9, 2026
Drunk Shakespeare: Drunk Dracula (21+ Event)
Downtown, the Loop & West Loop
A gothic comedy remixes Dracula with an audience-facing, adults-only Shakespeare format.
Limited Run
#9Runs through Oct 9, 2026 · Limited Run
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event)
A gothic comedy remixes Dracula with an audience-facing, adults-only Shakespeare format.
Add to calendar#10
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
#10September 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 calendarMore this weekend
#11
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
Lincoln Park, Lakeview & Wrigleyville
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
One Day Only
#11Mon, 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#12
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
#12September 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 calendar#13
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleOct 2, 2026–Oct 18, 2026
Vladimir
Lincoln Park, Lakeview & Wrigleyville
Vladimir is listed for Chicago this weekend.
Limited Run
#13Oct 2, 2026–Oct 18, 2026 · Limited Run
Theater Wit, Lincoln Park, Lakeview & Wrigleyville#14
Music Box Theatre, Southport Corridor, LakeviewSunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM$20 individual programs
Cinema Femme Short Film Festival 2026
Southport Corridor, Lakeview
The festival opens Sunday, then pairs a panel with two shorts programs.
One Weekend Only
#14Sunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM · One Weekend Only
Music Box Theatre, Southport Corridor, LakeviewCinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
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#15
Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM
Music Theater Works Presents: Escape to Margaritaville
9501 Skokie Blvd, Evanston & Oak Park
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
One Weekend Only
#15Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM · One Weekend Only
Music Theater Works Presents: Escape to Margaritaville
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
Add to calendar#16
Green Mill Cocktail Lounge, UptownKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsSaturdays at 3pm (doors 1pm); no end date announcedFREE
The Paper Machete
Green Mill Cocktail Lounge, Uptown
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
FreeLimited Run
#16Saturdays at 3pm (doors 1pm); no end date announced · Limited Run
Green Mill Cocktail Lounge, UptownKenneth 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#17
Music Box Theatre, Southport Corridor, LakeviewMonday, October 12, 2026 · 7 PM; post-film director Q&A$15 general admission
Begotten: New Restoration with E. Elias Merhige
Southport Corridor, Lakeview
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Limited Run
#17Monday, October 12, 2026 · 7 PM; post-film director Q&A · Limited Run
Music Box Theatre, Southport Corridor, LakeviewBegotten: 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#18
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 7:00pm
Robby Hoffman – Live on Tour
Lincoln Park, Lakeview & Wrigleyville
Comedian Robby Hoffman brings a headlining stand-up tour to the Vic Theatre.
One Day Only
#18Fri, Oct 9, 2026 · 7:00pm · One Day Only
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleRobby Hoffman – Live on Tour
Comedian Robby Hoffman brings a headlining stand-up tour to the Vic Theatre.
Add to calendar#19
Park West, Lincoln ParkSun, Oct 11, 2026 · 7:00pm
Kanan Gill: Not This Again
Park West, Lincoln Park
Comedian Kanan Gill brings a brand-new stand-up show to Park West.
One Day Only
#19Sun, Oct 11, 2026 · 7:00pm · One Day Only
Park West, Lincoln ParkKanan Gill: Not This Again
Comedian Kanan Gill brings a brand-new stand-up show to Park West.
Add to calendar#20
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
#20September 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 calendar#21
Douglass Park, North Lawndale, Pilsen, West Town & the West SideFriday, October 9, 2026 · 6–8 PMFREE
The Heart of the Story at Douglass
Pilsen, West Town & the West Side
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
FreeOne Day Only
#21Friday, October 9, 2026 · 6–8 PM · One Day Only
Douglass Park, North Lawndale, Pilsen, West Town & the West SideThe Heart of the Story at Douglass
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
Add to calendar#22
The Factory TheaterOct 9, 2026–Oct 18, 2026$30
The Factory Theater Presents the World Premiere of “Radical Futures”
The Factory Theater
The Factory Theater Presents the World Premiere of “Radical Futures” is listed for Chicago this.
Limited Run
#22Oct 9, 2026–Oct 18, 2026 · Limited Run
The Factory TheaterThe Factory Theater Presents the World Premiere of “Radical Futures”
The Factory Theater Presents the World Premiere of “Radical Futures” is listed for Chicago this.
Add to calendar#23
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsAugust 19–October 18, 2026Tickets via Drury Lane box of…
The Buddy Holly Story
Oakbrook Terrace, Far Suburbs
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Limited Run
#23August 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#24
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
#24October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareAbout this list
Stumblday's hand-checked ranking of the best date night in Chicago over Columbus Day weekend 2026 (Oct 10–12): 81 picks, refreshed weekly.
