Stumblday's hand-checked ranking of the best things to do in Chicago in September 2026: 144 picks, refreshed weekly. The month's biggest events, exhibitions and long runs in one ranked list, including every published weekend (Sep 11–13 · Sep 18–20 · Sep 25–27).
637 South Dearborn St., Chicago, IL., Downtown, the Loop & West LoopBrowse independent booksellers and hear authors at the free Printers Row Lit Fest, with more than 70 literary programs.
637 South Dearborn St., Chicago, IL., Downtown, the Loop & West LoopBrowse independent booksellers and hear authors at the free Printers Row Lit Fest, with more than 70 literary programs.
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.
Harris Theater Rooftop, Downtown, the Loop & West LoopChristine Harrison Frei · CC BY-SA 4.0 · Wikimedia CommonsChicago 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 LoopChristine Harrison Frei · CC BY-SA 4.0 · Wikimedia CommonsChicago Gourmet pairs its chef-led festival with a dance-inspired theme, including events at the Harris Theater Rooftop.
Ravenswood Industrial Corridor, Andersonville, Uptown & Lincoln SquareFollow Ravenswood ArtWalk through studios and galleries, then browse 80-plus makers with music along the industrial corridor.
Ravenswood Industrial Corridor, Andersonville, Uptown & Lincoln SquareFollow Ravenswood ArtWalk through studios and galleries, then browse 80-plus makers with music along the industrial corridor.
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.
National Museum of Mexican Art, Pilsen, West Town & the West SideNutmegger at English Wikipedia · Public domain · Wikimedia CommonsAuthors, photography and music shape Pilsen Day across the National Museum of Mexican Art and Thalia Hall.
National Museum of Mexican Art, Pilsen, West Town & the West SideNutmegger at English Wikipedia · Public domain · Wikimedia CommonsAuthors, photography and music shape Pilsen Day across the National Museum of Mexican Art and Thalia Hall.
Division Street between Damen and Ashland, Wicker Park, Logan Square, Wicker Park & BucktownPayton Chung from DCA, USA · CC BY 2.0 · Wikimedia CommonsBrowse 400-plus artists on Division Street, from handmade ceramics to jewelry and prints at Renegade’s outdoor fair.
Division Street between Damen and Ashland, Wicker Park, Logan Square, Wicker Park & BucktownPayton Chung from DCA, USA · CC BY 2.0 · Wikimedia CommonsBrowse 400-plus artists on Division Street, from handmade ceramics to jewelry and prints at Renegade’s outdoor fair.
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.
Western Avenue in Beverly/Morgan Park, Hyde Park, Bronzeville & the South SideDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsVisit artist studios, a handmade market and public art across Beverly and Morgan Park during the Beverly Art Walk.
Western Avenue in Beverly/Morgan Park, Hyde Park, Bronzeville & the South SideDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsVisit artist studios, a handmade market and public art across Beverly and Morgan Park during the Beverly Art Walk.
United Center, Pilsen, West Town & the West SideDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsRobyn and Peaches share the United Center bill as the Sexistential Tour brings Swedish pop back to a Chicago arena stage.
United Center, Pilsen, West Town & the West SideDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsRobyn and Peaches share the United Center bill as the Sexistential Tour brings Swedish pop back to a Chicago arena stage.
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.
Multiple Hyde Park venues, Hyde Park, Bronzeville & the South SideTizmsound · CC BY-SA 3.0 · 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 SideTizmsound · CC BY-SA 3.0 · Wikimedia CommonsHear Chicago jazz across neighborhood stages, with an anniversary band, intimate sets and a late solo performance by Joshua Redman.
Grant Park, Downtown, the Loop & West LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsEl Grito fills Grant Park’s Butler Field with Mexican music, food, an artisan mercado and family activities.
Grant Park, Downtown, the Loop & West LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsEl Grito fills Grant Park’s Butler Field with Mexican music, food, an artisan mercado and family activities.
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.
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.
Dawes Park, Evanston, Evanston & Oak ParkNick Number · CC BY 4.0 · Wikimedia CommonsTrampled by Turtles and Indigo Girls lead two days of folk music and artist conversations on Evanston’s lakefront.
Dawes Park, Evanston, Evanston & Oak ParkNick Number · CC BY 4.0 · Wikimedia CommonsTrampled by Turtles and Indigo Girls lead two days of folk music and artist conversations on Evanston’s lakefront.
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.
Multiple Chicago venuesWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsFollow free international music performances across Chicago, from an afternoon park gathering to late club shows and a closing outdoor celebration.
Multiple Chicago venuesWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsFollow free international music performances across Chicago, from an afternoon park gathering to late club shows and a closing outdoor celebration.
Wicker Park, Logan Square, Wicker Park & BucktownDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThirty-two juried artists line Wicker Park’s shady paths for a fair built around looking closely at the work.
Wicker Park, Logan Square, Wicker Park & BucktownDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsThirty-two juried artists line Wicker Park’s shady paths for a fair built around looking closely at the work.
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.
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvillePelican from Tokyo, Japan · CC BY-SA 4.0 · Wikimedia CommonsFall Fest turns Lincoln Park Zoo into a free autumn celebration all morning into evening.
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvillePelican from Tokyo, Japan · CC BY-SA 4.0 · Wikimedia CommonsFall Fest turns Lincoln Park Zoo into a free autumn celebration all morning into evening.
United Center, Pilsen, West Town & the West SideEva Rinaldi · CC BY-SA 2.0 · Wikimedia CommonsEric Clapton and Jimmie Vaughan bring a guitar-centered bill to United Center, backed by a full touring ensemble.
United Center, Pilsen, West Town & the West SideEva Rinaldi · CC BY-SA 2.0 · Wikimedia CommonsEric Clapton and Jimmie Vaughan bring a guitar-centered bill to United Center, backed by a full touring ensemble.
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.
NOW Arena, 5333 Prairie Stone Parkway, Far SuburbsKen Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia CommonsAEW’s All Out returns to NOW Arena for an evening of professional wrestling in Hoffman Estates.
NOW Arena, 5333 Prairie Stone Parkway, Far SuburbsKen Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia CommonsAEW’s All Out returns to NOW Arena for an evening of professional wrestling in Hoffman Estates.