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Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsDowntown, the Loop & West Loop
The Chicago Marathon sends runners through the city before a Grant Park finish.
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsThe Chicago Marathon sends runners through the city before a Grant Park finish.
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Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleFall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
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Humboldt (Alexander Von) Park, Humboldt Park, Logan Square, Wicker Park & BucktownGazeboJake · CC0 · Wikimedia CommonsLogan Square, Wicker Park & Bucktown
Eight companies dance free and outdoors in Humboldt Park, from Afro-Latin to folkloric styles.
Humboldt (Alexander Von) Park, Humboldt Park, Logan Square, Wicker Park & BucktownGazeboJake · CC0 · Wikimedia CommonsEight companies dance free and outdoors in Humboldt Park, from Afro-Latin to folkloric styles.
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Jonquil Park, Lincoln ParkWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsJonquil Park, Lincoln Park
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
Jonquil Park, Lincoln ParkWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsThe 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
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Butler Field, Grant Park, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsDowntown, the Loop & West Loop
The part of marathon Sunday in Grant Park that needs no bib, to 4pm.
Butler Field, Grant Park, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThe part of marathon Sunday in Grant Park that needs no bib, to 4pm.
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Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsGlencoe, Far Suburbs
Seventy-five giant pumpkins, live carving and performers light a three-night garden walk.
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsSeventy-five giant pumpkins, live carving and performers light a three-night garden walk.
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Logan Center for the Arts, Hyde ParkCharter6281 · CC BY-SA 4.0 · Wikimedia CommonsLogan Center for the Arts, Hyde Park
A curator-led 11 a.m. walkthrough adds a timed hook to this Obama-era art survey.
Logan Center for the Arts, Hyde ParkCharter6281 · CC BY-SA 4.0 · Wikimedia CommonsA curator-led 11 a.m. walkthrough adds a timed hook to this Obama-era art survey.
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The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopA new play runs select dates at Chicago Shakespeare's Navy Pier stage.
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Grant Park, The LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsGrant Park, The Loop
The official 5K sends marathon-weekend runners through a downtown course.
Grant Park, The LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsThe official 5K sends marathon-weekend runners through a downtown course.
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Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West LoopDowntown, the Loop & West Loop
TenderFest @ East End Plaza at Navy Pier
Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West Loop
Logan Center for the Arts, Hyde ParkLogan Center for the Arts, Hyde Park
An octet unheard since 1897 returns in a one-night University of Chicago performance.
Logan Center for the Arts, Hyde ParkAn octet unheard since 1897 returns in a one-night University of Chicago performance.
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Park West, Lincoln ParkPark West, Lincoln Park
National Park After Dark: Your Neck of the Woods Tour
Park West, Lincoln ParkNational Park After Dark: Your Neck of the Woods Tour
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Smart Museum of Art, Hyde ParkSmart Museum of Art, Hyde Park
A teamLab member and the exhibition curator discuss the collective’s creative practice.
Smart Museum of Art, Hyde ParkA teamLab member and the exhibition curator discuss the collective’s creative practice.
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Chicago History Museum, Lincoln ParkGoldnpuppy · CC BY-SA 3.0 · Wikimedia CommonsChicago History Museum, Lincoln Park
Illinois residents get free Monday access to the museum’s permanent and temporary shows.
Chicago History Museum, Lincoln ParkGoldnpuppy · CC BY-SA 3.0 · Wikimedia CommonsIllinois residents get free Monday access to the museum’s permanent and temporary shows.
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Harrison (Carter) Park, PilsenHarrison (Carter) Park, Pilsen
A free afternoon of music, dance and stories for Indigenous Peoples' Day in Harrison Park.
Harrison (Carter) Park, PilsenA free afternoon of music, dance and stories for Indigenous Peoples' Day in Harrison Park.
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Navy Pier, 600 E Grand Ave, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Punchis Punchis brings its Banda Rave Experience to Navy Pier.
Navy Pier, 600 E Grand Ave, Downtown, the Loop & West LoopPunchis Punchis brings its Banda Rave Experience to Navy Pier.
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Eckhart (Bernard) Park, West Town, Logan Square, Wicker Park & BucktownLogan Square, Wicker Park & Bucktown
Transilience: Chicago Trans Pride Festival at Eckhart has enough weekend energy to earn a spot on the board.
Eckhart (Bernard) Park, West Town, Logan Square, Wicker Park & BucktownTransilience: Chicago Trans Pride Festival at Eckhart has enough weekend energy to earn a spot on the board.
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Chicago Children’s Museum, Navy Pier, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
A story lounge and native Illinois seed-ball activity mark Indigenous People’s Day.
Chicago Children’s Museum, Navy Pier, Downtown, the Loop & West LoopA story lounge and native Illinois seed-ball activity mark Indigenous People’s Day.
Add to calendarLincoln Park, Lakeview & Wrigleyville
Failure plays an 18-and-over show at Park West.
Park West, Lincoln ParkPark West, Lincoln Park
Comedian Kanan Gill brings a brand-new stand-up show to Park West.
Park West, Lincoln ParkComedian Kanan Gill brings a brand-new stand-up show to Park West.
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Douglass Park, North Lawndale, Pilsen, West Town & the West SidePilsen, West Town & the West Side
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
Douglass Park, North Lawndale, Pilsen, West Town & the West SideCerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
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The Alley Cat, Wicker ParkThe Alley Cat, Wicker Park
Stray Chef Sundays: Donald Young has enough weekend energy to earn a spot on the board.
The Alley Cat, Wicker ParkStray Chef Sundays: Donald Young has enough weekend energy to earn a spot on the board.
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AIDS Garden Chicago, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Really Really Free Market has enough weekend energy to earn a spot on the board.
AIDS Garden Chicago, Lincoln Park, Lakeview & WrigleyvilleReally Really Free Market has enough weekend energy to earn a spot on the board.
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Taan, Humboldt Park, Pilsen, West Town & the West SidePilsen, West Town & the West Side
Taan is listed for Chicago this weekend.
Taan, Humboldt Park, Pilsen, West Town & the West SideStumblday's hand-checked ranking of the best outdoors in Chicago over Columbus Day weekend 2026 (Oct 10–12): 33 picks, refreshed weekly.
