Stumblday's hand-checked ranking of the best music in Chicago the weekend of Sep 25–27, 2026: 57 picks, refreshed weekly.
57 picks · checked Sep 21
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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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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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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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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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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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.
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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Credit Union 1 Amphitheatre, Far SuburbsBryson Tiller brings the trap-R&B sound behind “Don’t” and Trapsoul to Tinley Park on The Neo Trapsoul Tour.
Credit Union 1 Amphitheatre, Far SuburbsBryson Tiller brings the trap-R&B sound behind “Don’t” and Trapsoul to Tinley Park on The Neo Trapsoul Tour.
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Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsSibelius’s Seventh and Shostakovich’s Fourth meet in a two-symphony CSO program led by Klaus Mäkelä.
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsSibelius’s Seventh and Shostakovich’s Fourth meet in a two-symphony CSO program led by Klaus Mäkelä.
Add to calendarSan Holo brings an 18+ electronic set to Radius night.
Copernicus Center, 5216 W. Lawrence Ave, Logan Square, Wicker Park & BucktownGOT7 leader JAY B brings his solo tape: roots show to the Gateway Theater at Copernicus Center.
Copernicus Center, 5216 W. Lawrence Ave, Logan Square, Wicker Park & BucktownGOT7 leader JAY B brings his solo tape: roots show to the Gateway Theater at Copernicus Center.
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The Salt Shed, Logan Square, Wicker Park & BucktownCavetown and Chloe Moriondo bring the Running With Scissors Tour into the Salt Shed’s indoor room.
The Salt Shed, Logan Square, Wicker Park & BucktownCavetown and Chloe Moriondo bring the Running With Scissors Tour into the Salt Shed’s indoor room.
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Riviera Theatre, Andersonville, Uptown & Lincoln SquarePaul R. Burley · CC BY-SA 4.0 · Wikimedia CommonsMichael Shannon, Jason Narducy and friends play R.E.M.’s Lifes Rich Pageant at the Riviera.
Riviera Theatre, Andersonville, Uptown & Lincoln SquarePaul R. Burley · CC BY-SA 4.0 · Wikimedia CommonsMichael Shannon, Jason Narducy and friends play R.E.M.’s Lifes Rich Pageant at the Riviera.
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The Salt Shed (Fairgrounds, outdoors), Goose Island, Logan Square, Wicker Park & BucktownClassic-sounding soul, Latin grooves and sister harmonies, outdoors on the Salt Shed Fairgrounds.
The Salt Shed (Fairgrounds, outdoors), Goose Island, Logan Square, Wicker Park & BucktownClassic-sounding soul, Latin grooves and sister harmonies, outdoors on the Salt Shed Fairgrounds.
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Kehrein Center for the Arts, Austin, Pilsen, West Town & the West SideCabo Verdean singer Elida Almeida headlines a free World Music Festival performance at the Kehrein Center.
Kehrein Center for the Arts, Austin, Pilsen, West Town & the West SideCabo Verdean singer Elida Almeida headlines a free World Music Festival performance at the Kehrein Center.
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Rosemont Theatre, 5400 North River Road, Evanston & Oak ParkMatute plays the Rosemont Theatre for one night only on its current tour.
Rosemont Theatre, 5400 North River Road, Evanston & Oak ParkMatute plays the Rosemont Theatre for one night only on its current tour.
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Radius Chicago, South Loop, Pilsen, West Town & the West SideIan Asher headlines a late Radius show with Nate Band and Kala opening.
Radius Chicago, South Loop, Pilsen, West Town & the West SideIan Asher headlines a late Radius show with Nate Band and Kala opening.
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Thalia Hall, Pilsen, West Town & the West SidePaula Cole marks 30 years of This Fire with a Thalia Hall anniversary show.
Thalia Hall, Pilsen, West Town & the West SidePaula Cole marks 30 years of This Fire with a Thalia Hall anniversary show.
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Riviera Theatre, Andersonville, Uptown & Lincoln SquareThe Garden – Bootleg Tour has enough weekend energy to earn a spot on the board.
Riviera Theatre, Andersonville, Uptown & Lincoln SquareThe Garden – Bootleg Tour has enough weekend energy to earn a spot on the board.
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Wagner Stage, Hyde Park, Bronzeville & the South SideMarquis Hill, Makaya McCraven, Junius Paul and Joel Ross reunite for the festival's 20th.
Wagner Stage, Hyde Park, Bronzeville & the South SideMarquis Hill, Makaya McCraven, Junius Paul and Joel Ross reunite for the festival's 20th.
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Rockefeller Memorial Chapel, Hyde Park, Bronzeville & the South SideStar saxophonist Joshua Redman plays an unaccompanied late-night set inside Rockefeller Chapel.
Rockefeller Memorial Chapel, Hyde Park, Bronzeville & the South SideStar saxophonist Joshua Redman plays an unaccompanied late-night set inside Rockefeller Chapel.
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