Stumblday's hand-checked ranking of the best things to do in Chicago the weekend of Sep 18–20, 2026: 50 picks, refreshed weekly. Concerts, festivals, art, markets, and free outdoor events.
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50 picks · checked Sep 10
Douglass Park, 1401 S Sacramento Dr., Pilsen, West Town & the West SideE.C. Kropp Co. · Public domain · Wikimedia CommonsTool, Morrissey and Nas lead Riot Fest’s Saturday lineup in Douglass Park.
Douglass Park, 1401 S Sacramento Dr., Pilsen, West Town & the West SideE.C. Kropp Co. · Public domain · Wikimedia CommonsTool, Morrissey and Nas lead Riot Fest’s Saturday lineup in Douglass Park.
Wrightwood Park, Lincoln Park, Lakeview & WrigleyvilleVictor Grigas · CC BY-SA 3.0 · Wikimedia CommonsExplore Chicago’s cultural variety one dumpling at a time at the Chicago Cultural Alliance’s food festival.
Wrightwood Park, Lincoln Park, Lakeview & WrigleyvilleVictor Grigas · CC BY-SA 3.0 · Wikimedia CommonsExplore Chicago’s cultural variety one dumpling at a time at the Chicago Cultural Alliance’s food festival.
Hamilton Park and Cultural Center, Hyde Park, Bronzeville & the South SideChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia CommonsEnglewood Jazz Festival brings original music and intergenerational ensembles to Hamilton Park for its 27th edition.
Hamilton Park and Cultural Center, Hyde Park, Bronzeville & the South SideChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia CommonsEnglewood Jazz Festival brings original music and intergenerational ensembles to Hamilton Park for its 27th edition.
United Center, 1901 W Madison, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsPhoebe Bridgers brings the Lost Tour to the United Center with special guest Alex G.
United Center, 1901 W Madison, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsPhoebe Bridgers brings the Lost Tour to the United Center with special guest Alex G.
Navy Pier, Streeterville, Downtown, the Loop & West LoopMojnsen · CC BY-SA 4.0 · Wikimedia CommonsCommon, ballet and comedy share Navy Pier’s free festival of Chicago performers across five stages.
Navy Pier, Streeterville, Downtown, the Loop & West LoopMojnsen · CC BY-SA 4.0 · Wikimedia CommonsCommon, ballet and comedy share Navy Pier’s free festival of Chicago performers across five stages.
Shedd Aquarium, Downtown, the Loop & West LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsDance salsa, cumbia and merengue at Shedd’s Ritmo del Mar, with aquarium exhibits included in the evening ticket.
Shedd Aquarium, Downtown, the Loop & West LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsDance salsa, cumbia and merengue at Shedd’s Ritmo del Mar, with aquarium exhibits included in the evening ticket.
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsHilary Hahn plays Mendelssohn with the CSO, framed by Schumann and Dvořák under Petr Popelka.
Orchestra Hall, Symphony Center, 220 S. Michigan Ave., Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsHilary Hahn plays Mendelssohn with the CSO, framed by Schumann and Dvořák under Petr Popelka.
North BroadwayPaul R. Burley · CC BY-SA 4.0 · Wikimedia CommonsBrowse 150 juried artists along Broadway at the Lakeview East Festival of the Arts, with music, food and family activities.
North BroadwayPaul R. Burley · CC BY-SA 4.0 · Wikimedia CommonsBrowse 150 juried artists along Broadway at the Lakeview East Festival of the Arts, with music, food and family activities.
Eataly Chicago, Downtown, the Loop & West LoopTony Webster · CC BY-SA 3.0 · Wikimedia CommonsExplore Eataly’s Septemberfest through more than 30 chef-curated bites and 15 stations pouring Italian drinks.
Eataly Chicago, Downtown, the Loop & West LoopTony Webster · CC BY-SA 3.0 · Wikimedia CommonsExplore Eataly’s Septemberfest through more than 30 chef-curated bites and 15 stations pouring Italian drinks.
Garfield Park Field House. 100 N. Central Park Avenue, Chicago, IL, 60624Disabled Chicago artists and Garfield Park student composers share a free art-and-music showcase at the field house.
Garfield Park Field House. 100 N. Central Park Avenue, Chicago, IL, 60624Disabled Chicago artists and Garfield Park student composers share a free art-and-music showcase at the field house.
Haymarket House, Andersonville, Uptown & Lincoln SquareDan Leonard · CC0 · Wikimedia CommonsDance, local artists and climate action come together at Uptown Rhythm Festival at Haymarket House.
Haymarket House, Andersonville, Uptown & Lincoln SquareDan Leonard · CC0 · Wikimedia CommonsDance, local artists and climate action come together at Uptown Rhythm Festival at Haymarket House.
Roscoe Street — Damen to Leavitt, Roscoe Village, Lincoln Park, Lakeview & Wrigleyvillew_lemay · CC BY-SA 2.0 · Wikimedia CommonsClassic cars, two music stages and a children’s area turn Roscoe Street into a weekend festival.
Roscoe Street — Damen to Leavitt, Roscoe Village, Lincoln Park, Lakeview & Wrigleyvillew_lemay · CC BY-SA 2.0 · Wikimedia CommonsClassic cars, two music stages and a children’s area turn Roscoe Street into a weekend festival.
Lyric Opera House, Loop, Downtown, the Loop & West LoopRaymond Britt · CC BY-SA 3.0 · Wikimedia CommonsJoffrey premieres John Neumeier’s Liliom in Chicago, pairing narrative ballet with Michel Legrand’s jazz-inflected score.
Lyric Opera House, Loop, Downtown, the Loop & West LoopRaymond Britt · CC BY-SA 3.0 · Wikimedia CommonsJoffrey premieres John Neumeier’s Liliom in Chicago, pairing narrative ballet with Michel Legrand’s jazz-inflected score.
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopDuke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopDuke Ellington’s music carries Twelfth Night’s disguises and romantic mix-ups into 1930s Harlem in Play On!
Participating Chicago galleries and institutions, CitywideU.S. Army · CC BY 2.0 · Wikimedia CommonsGallery openings, artist conversations and performances connect more than 50 spaces during Chicago Exhibition Week.
Participating Chicago galleries and institutions, CitywideU.S. Army · CC BY 2.0 · Wikimedia CommonsGallery openings, artist conversations and performances connect more than 50 spaces during Chicago Exhibition Week.
Art Institute of Chicago, Regenstein Hall, Downtown, the Loop & West LoopPedro Ribeiro Simões from Lisboa, Portugal · CC BY 2.0 · Wikimedia CommonsFollow seven decades of Willem de Kooning’s drawing through more than 200 works at the Art Institute.
Art Institute of Chicago, Regenstein Hall, Downtown, the Loop & West LoopPedro Ribeiro Simões from Lisboa, Portugal · CC BY 2.0 · Wikimedia CommonsFollow seven decades of Willem de Kooning’s drawing through more than 200 works at the Art Institute.
Soldier Field, 1410 S. Museum Campus Drive, Downtown, the Loop & West LoopRyan Dickey from Evanston, IL / Chicago, United States · CC BY 2.0 · Wikimedia CommonsThe Bears meet Minnesota at Soldier Field, putting a familiar divisional matchup on Chicago’s home turf.
Soldier Field, 1410 S. Museum Campus Drive, Downtown, the Loop & West LoopRyan Dickey from Evanston, IL / Chicago, United States · CC BY 2.0 · Wikimedia CommonsThe Bears meet Minnesota at Soldier Field, putting a familiar divisional matchup on Chicago’s home turf.
Museum of Contemporary Art Chicago, Downtown, the Loop & West LoopGregory Ford Henderson · CC BY-SA 4.0 · Wikimedia CommonsDancehall and reggaetón meet contemporary art in the MCA’s look at Caribbean music, resistance and joy.
Museum of Contemporary Art Chicago, Downtown, the Loop & West LoopGregory Ford Henderson · CC BY-SA 4.0 · Wikimedia CommonsDancehall and reggaetón meet contemporary art in the MCA’s look at Caribbean music, resistance and joy.
The Alley Cat, Wicker Park, Logan Square, Wicker Park & BucktownCarol M. Highsmith · Public domain · Wikimedia CommonsBeity chef Ryan Fakih brings his Lebanese culinary perspective to The Alley Cat’s guest-dish and deviled-egg collaboration.
The Alley Cat, Wicker Park, Logan Square, Wicker Park & BucktownCarol M. Highsmith · Public domain · Wikimedia CommonsBeity chef Ryan Fakih brings his Lebanese culinary perspective to The Alley Cat’s guest-dish and deviled-egg collaboration.
Anthenaeum Theater, Lincoln Park, Lakeview & WrigleyvilleChicago Story Fest blends journalists’ stories with film, dance and live music at the Athenaeum.
Anthenaeum Theater, Lincoln Park, Lakeview & WrigleyvilleChicago Story Fest blends journalists’ stories with film, dance and live music at the Athenaeum.
James M. Nederlander Theatre, 24 W Randolph, Downtown, the Loop & West LoopAaron Volkening · CC BY 2.0 · Wikimedia CommonsBaby and Johnny’s summer romance reaches the Nederlander with live music in Dirty Dancing: The Musical.
James M. Nederlander Theatre, 24 W Randolph, Downtown, the Loop & West LoopAaron Volkening · CC BY 2.0 · Wikimedia CommonsBaby and Johnny’s summer romance reaches the Nederlander with live music in Dirty Dancing: The Musical.
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsTrade playground nostalgia for karaoke, a live band and retro DJ sets at Lincoln Park Zoo’s adults-only ’80s vs. ’90s night.
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsTrade playground nostalgia for karaoke, a live band and retro DJ sets at Lincoln Park Zoo’s adults-only ’80s vs. ’90s night.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThe comedian behind Father and The Intruder brings The Big Bowl Tour to the Chicago Theatre: Atsuko Okatsuka, in person.
The Chicago Theatre, 175 N State St, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThe comedian behind Father and The Intruder brings The Big Bowl Tour to the Chicago Theatre: Atsuko Okatsuka, in person.
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West LoopA pumpkin-themed pop-up runs at Jack's Pumpkin Pop-Up downtown.
Jack's Pumpkin Pop-Up, Downtown Chicago, Downtown, the Loop & West LoopA pumpkin-themed pop-up runs at Jack's Pumpkin Pop-Up downtown.