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Stumblday's hand-checked ranking of the best things to do in Chicago in October 2026: 207 picks, refreshed weekly. The month's biggest events, exhibitions and long runs in one ranked list, including every published weekend (Oct 30 – Nov 1).
North Halsted Street, Northalsted, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Northalsted's 30th Halloween parade expands into an all-day block party before the costumed procession.
North Halsted Street, Northalsted, Lincoln Park, Lakeview & WrigleyvilleNorthalsted's 30th Halloween parade expands into an all-day block party before the costumed procession.
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26th Street corridor, Little Village, Pilsen, West Town & the West SidePilsen, West Town & the West Side
Little Village marks Día de los Muertos with a two-day neighborhood celebration along 26th Street.
26th Street corridor, Little Village, Pilsen, West Town & the West SideLittle Village marks Día de los Muertos with a two-day neighborhood celebration along 26th Street.
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Taan, Humboldt Park, Pilsen, West Town & the West SideTaan, Humboldt Park, Pilsen, West Town & the West Side
Lincoln Park Zoo, Lincoln ParkLincoln Park Zoo, Lincoln Park
Fall Fest at Lincoln Park Zoo.
Lincoln Park Zoo, Lincoln Park
Music Box Theatre, LakeviewMusic Box Theatre, Lakeview
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
Music Box Theatre, LakeviewMusic Box of Horrors: The Final Chapter is listed for Chicago this weekend.
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Goodman Theatre, Owen Theatre, The LoopOwen Theatre, The Loop
Three friends investigate a classmate’s quinceañera disappearance in this comic thriller.
Goodman Theatre, Owen Theatre, The LoopThree friends investigate a classmate’s quinceañera disappearance in this comic thriller.
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Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Jack's Pumpkin Pop-Up at Jack's Pumpkin Pop-Up.
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West Loop
Six Flags Great America, Gurnee, Far SuburbsGurnee, Far Suburbs
Six Flags fills select fall nights with haunted mazes, scare zones and live shows.
Six Flags Great America, Gurnee, Far SuburbsSix Flags fills select fall nights with haunted mazes, scare zones and live shows.
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Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Topdog/Underdog at Steppenwolf Downstairs Theater.
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & Wrigleyville
American Writers Museum, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
American Prophets: Writers, Religion and Culture at American Writers Museum.
American Writers Museum, Downtown, the Loop & West LoopAmerican Prophets: Writers, Religion and Culture at American Writers Museum.
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The Ritz-Carlton, Chicago 160 E Pearson St 12th Floor Chicago, IL 60611Chicago 160 E Pearson St 12th Floor Chicago, IL 60611
Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago at The Ritz-Carlton.
The Ritz-Carlton, Chicago 160 E Pearson St 12th Floor Chicago, IL 60611Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago at The Ritz-Carlton.
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Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Theater of the Mind at Reid Murdoch Building – 333 N LaSalle.
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Kokandy Productions Jekyll & Hyde (Chicago) at Broadway Playhouse at Water Tower Place.
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West LoopKokandy Productions Jekyll & Hyde (Chicago) at Broadway Playhouse at Water Tower Place.
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Theater Wit, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Vladimir at Theater Wit.
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleEach October weekend's list lands the Friday before it, one email every Friday. Unsubscribe anytime.
CinespaceCinespace
Serial Killer: The Exhibition at Cinespace.
Cinespace
The Second City, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Baby Wants Candy! The Original Completely Improvised Musical at The Second City.
The Second City, Lincoln Park, Lakeview & WrigleyvilleBaby Wants Candy! The Original Completely Improvised Musical at The Second City.
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The Den Theatre, Logan Square, Wicker Park & BucktownLogan Square, Wicker Park & Bucktown
Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire” at The Den Theatre.
The Den Theatre, Logan Square, Wicker Park & BucktownRefracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire” at The Den Theatre.
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Oil Lamp TheaterOil Lamp Theater
Oil Lamp Theater Presents “Dial M for Murder” at Oil Lamp Theater.
Oil Lamp TheaterOil Lamp Theater Presents “Dial M for Murder” at Oil Lamp Theater.
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Chicago’s First Lady CruisesChicago’s First Lady Cruises
Chicago By Night River & Lake at Chicago’s First Lady Cruises.
Chicago’s First Lady CruisesChicago By Night River & Lake at Chicago’s First Lady Cruises.
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Stars and Garters TheaterStars and Garters Theater
The Séance: Live (and dead) in Chicago at Stars and Garters Theater.
Stars and Garters TheaterThe Séance: Live (and dead) in Chicago at Stars and Garters Theater.
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The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
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Annoyance Theatre & BarAnnoyance Theatre & Bar
Comedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
Annoyance Theatre & BarComedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
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Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United StatesIL 60611, United States
INCREDIBLE INSECTS: Interactive Live Bug Exhibit at Navy Pier, 600 E Grand Ave, Chicago, IL 60611.
Navy Pier, 600 E Grand Ave, Chicago, IL 60611, United StatesINCREDIBLE INSECTS: Interactive Live Bug Exhibit at Navy Pier, 600 E Grand Ave, Chicago, IL 60611.
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Redtwist TheatreRedtwist Theatre
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” at Redtwist Theatre.
Redtwist TheatreRedtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” at Redtwist Theatre.
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