Stumblday's hand-checked ranking of the best things to do in Chicago the weekend of Sep 25–27, 2026: 301 picks, refreshed weekly. Concerts, festivals, art, markets, and free outdoor events.
301 picks · checked Sep 21
Multiple Hyde Park venues, Hyde Park, Bronzeville & the South SideJoe Passe · CC BY-SA 2.0 · Wikimedia CommonsHear Chicago jazz across neighborhood stages, with an anniversary band, intimate sets and a late solo performance by Joshua Redman.
Multiple Hyde Park venues, Hyde Park, Bronzeville & the South SideJoe Passe · CC BY-SA 2.0 · Wikimedia CommonsHear Chicago jazz across neighborhood stages, with an anniversary band, intimate sets and a late solo performance by Joshua Redman.
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United Center, 1901 W Madison, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsTeddy Swims brings his romantic confessionals and big pop hooks to the United Center, with Mac Ayres and MarcLo.
United Center, 1901 W Madison, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsTeddy Swims brings his romantic confessionals and big pop hooks to the United Center, with Mac Ayres and MarcLo.
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Medinah Country Club (Course No. 3), Medinah, Far SuburbsDan Perry · CC BY 2.0 · Wikimedia CommonsTop US golfers face an International side in loud, partisan team match play at Medinah.
Medinah Country Club (Course No. 3), Medinah, Far SuburbsDan Perry · CC BY 2.0 · Wikimedia CommonsTop US golfers face an International side in loud, partisan team match play at Medinah.
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The Chicago Theatre, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsSara Bareilles brings the Good Grief Tour to the Chicago Theatre for a Sunday concert in the downtown landmark.
The Chicago Theatre, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsSara Bareilles brings the Good Grief Tour to the Chicago Theatre for a Sunday concert in the downtown landmark.
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Huntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopDwightSchruteDunderMifflin · CC BY 4.0 · Wikimedia CommonsFoster the People’s indie pop meets a stage world of unraveling 1950s optimism at Northerly Island, with Goth Babe.
Huntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopDwightSchruteDunderMifflin · CC BY 4.0 · Wikimedia CommonsFoster the People’s indie pop meets a stage world of unraveling 1950s optimism at Northerly Island, with Goth Babe.
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Harris Theater Rooftop, Downtown, the Loop & West LoopChicago Gourmet pairs its chef-led festival with a dance-inspired theme, including events at the Harris Theater Rooftop.
Harris Theater Rooftop, Downtown, the Loop & West LoopChicago Gourmet pairs its chef-led festival with a dance-inspired theme, including events at the Harris Theater Rooftop.
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WWE, NXT and Lucha Libre AAA share the Worlds Collide billing at Allstate Arena.
WWE, NXT and Lucha Libre AAA share the Worlds Collide billing at Allstate Arena.
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Multiple Chicago venuesw_lemay · CC BY-SA 2.0 · Wikimedia CommonsFollow free international music performances across Chicago.
Multiple Chicago venuesw_lemay · CC BY-SA 2.0 · Wikimedia CommonsFollow free international music performances across Chicago.
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Ping Tom Memorial Park, Chinatown, Downtown, the Loop & West LoopTorsodog · CC BY-SA 3.0 · Wikimedia CommonsSix free hours of sound-system music under the 18th Street bridge in Chinatown.
Ping Tom Memorial Park, Chinatown, Downtown, the Loop & West LoopTorsodog · CC BY-SA 3.0 · Wikimedia CommonsSix free hours of sound-system music under the 18th Street bridge in Chinatown.
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Osaka Garden, Jackson Park, Hyde Park, Bronzeville & the South Sidezooey from Chicago, Illinois USA · CC BY 2.0 · Wikimedia CommonsMoon viewing after dark in Osaka Garden, with haiku readings and a calligraphy demo, all free.
Osaka Garden, Jackson Park, Hyde Park, Bronzeville & the South Sidezooey from Chicago, Illinois USA · CC BY 2.0 · Wikimedia CommonsMoon viewing after dark in Osaka Garden, with haiku readings and a calligraphy demo, all free.
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Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
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Rosemont Theatre, Evanston & Oak ParkZol87 from Chicago, Illinois, USA · CC BY-SA 4.0 · Wikimedia CommonsJuanes brings his 2026 world tour to Rosemont Theatre, with the JuanesTeban album shaping the tour’s context.
Rosemont Theatre, Evanston & Oak ParkZol87 from Chicago, Illinois, USA · CC BY-SA 4.0 · Wikimedia CommonsJuanes brings his 2026 world tour to Rosemont Theatre, with the JuanesTeban album shaping the tour’s context.
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Chicago Riverwalk, The Confluence, Downtown, the Loop & West LoopJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsFree on the Riverwalk: the Afro-Puerto Rican drum tradition salsa grew out of.
Chicago Riverwalk, The Confluence, Downtown, the Loop & West LoopJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsFree on the Riverwalk: the Afro-Puerto Rican drum tradition salsa grew out of.
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Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West LoopIIP Photo Archive · CC BY 2.0 · Wikimedia CommonsMike Dunn, DJ Heather and more close House Music is Home’s Navy Pier season with a free RSVP dance party.
Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West LoopIIP Photo Archive · CC BY 2.0 · Wikimedia CommonsMike Dunn, DJ Heather and more close House Music is Home’s Navy Pier season with a free RSVP dance party.
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NOW Arena, 5333 Prairie Stone Parkway, Far SuburbsAEW’s All Out returns to NOW Arena for an evening of professional wrestling in Hoffman Estates.
NOW Arena, 5333 Prairie Stone Parkway, Far SuburbsAEW’s All Out returns to NOW Arena for an evening of professional wrestling in Hoffman Estates.
Add to calendarPreseason hockey brings the Blackhawks and Blues to the United Center.
Preseason hockey brings the Blackhawks and Blues to the United Center.
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Metro, 3730 N. Clark St., Lincoln Park, Lakeview & WrigleyvilleStabbing Westward lead the 14th Cold Waves show at Metro, open to ages 18 and over.
Metro, 3730 N. Clark St., Lincoln Park, Lakeview & WrigleyvilleStabbing Westward lead the 14th Cold Waves show at Metro, open to ages 18 and over.
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Arie Crown Theater, Downtown, the Loop & West LoopLegendary comedian and actor Martin Lawrence plays one night live at Arie Crown Theater.
Arie Crown Theater, Downtown, the Loop & West LoopLegendary comedian and actor Martin Lawrence plays one night live at Arie Crown Theater.
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Chicago Cultural Center, Preston Bradley Hall, The Loop, Downtown, the Loop & West LoopGrant Henninger · CC BY-SA 4.0 · Wikimedia CommonsFree overnight Carnatic and Hindustani sets under the Tiffany dome, with L. Shankar around 1 a.m.
Chicago Cultural Center, Preston Bradley Hall, The Loop, Downtown, the Loop & West LoopGrant Henninger · CC BY-SA 4.0 · Wikimedia CommonsFree overnight Carnatic and Hindustani sets under the Tiffany dome, with L. Shankar around 1 a.m.
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Chicago Cultural Center, Downtown, the Loop & West LoopGrant Henninger · CC BY-SA 4.0 · Wikimedia CommonsAn immersive sound and visual piece built around taiko drum, saxophone, cello and bass.
Chicago Cultural Center, Downtown, the Loop & West LoopGrant Henninger · CC BY-SA 4.0 · Wikimedia CommonsAn immersive sound and visual piece built around taiko drum, saxophone, cello and bass.
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St. Alphonsus Church grounds, Lakeview, Lincoln Park, Lakeview & WrigleyvilleLeijaonate · CC BY-SA 4.0 · Wikimedia CommonsThree days of oompah bands, steins, bratwurst and polka dancing on the Lakeview church grounds.
St. Alphonsus Church grounds, Lakeview, Lincoln Park, Lakeview & WrigleyvilleLeijaonate · CC BY-SA 4.0 · Wikimedia CommonsThree days of oompah bands, steins, bratwurst and polka dancing on the Lakeview church grounds.
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Lyric Opera House, Loop, Downtown, the Loop & West LoopThe Joffrey Ballet brings Molnár's Liliom to the Lyric stage for select September performances.
Lyric Opera House, Loop, Downtown, the Loop & West LoopThe Joffrey Ballet brings Molnár's Liliom to the Lyric stage for select September performances.
Add to calendarA three-game Sox home series against the Rockies, with a day game to close the weekend.
A three-game Sox home series against the Rockies, with a day game to close the weekend.
Add to calendarSofi Tukker play the pavilion on Northerly Island for one night, with special guest Kungs.
Sofi Tukker play the pavilion on Northerly Island for one night, with special guest Kungs.
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