Stumblday's hand-checked ranking of the best free things to do in Chicago the weekend of Sep 25–27, 2026: 11 picks, refreshed weekly.
11 picks · checked Sep 10
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.
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.
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.
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.
Milwaukee Ave from North/Damen to Ashland, Logan Square, Wicker Park & BucktownDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsWalk Milwaukee Avenue without its usual through traffic during this Wicker Park and Bucktown street-opening pilot.
Milwaukee Ave from North/Damen to Ashland, Logan Square, Wicker Park & BucktownDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsWalk Milwaukee Avenue without its usual through traffic during this Wicker Park and Bucktown street-opening pilot.
Bronzeville Business Corridors, Hyde Park, Bronzeville & the South SideFollow local music into Bronzeville’s shops and restaurants as Summer Nights links neighborhood culture with its business corridors.
Bronzeville Business Corridors, Hyde Park, Bronzeville & the South SideFollow local music into Bronzeville’s shops and restaurants as Summer Nights links neighborhood culture with its business corridors.
2347 W Augusta Blvd, Chicago, IL 60622, Pilsen, West Town & the West SideSt. Helen celebrates twenty carnival years in Ukrainian Village with rides, food, music and neighborhood festivities.
2347 W Augusta Blvd, Chicago, IL 60622, Pilsen, West Town & the West SideSt. Helen celebrates twenty carnival years in Ukrainian Village with rides, food, music and neighborhood festivities.
National Public Housing Museum, Pilsen, West Town & the West SideRoosevelt, Franklin D. (Franklin Delano), 1882-1945 · Public domain · Wikimedia CommonsLydia Cheshewalla and Elise Paschen discuss place, memory and Osage perspectives at the National Public Housing Museum.
National Public Housing Museum, Pilsen, West Town & the West SideRoosevelt, Franklin D. (Franklin Delano), 1882-1945 · Public domain · Wikimedia CommonsLydia Cheshewalla and Elise Paschen discuss place, memory and Osage perspectives at the National Public Housing Museum.
Downtown Oak Park, Oak Park, Evanston & Oak ParkDavid Wilson from Oak Park, Illinois, USA · CC BY 2.0 · Wikimedia CommonsHead to downtown Oak Park for live music, local food and craft beer at a free autumn street festival.
Downtown Oak Park, Oak Park, Evanston & Oak ParkDavid Wilson from Oak Park, Illinois, USA · CC BY 2.0 · Wikimedia CommonsHead to downtown Oak Park for live music, local food and craft beer at a free autumn street festival.
Museum of Contemporary Photography, South Loop, Downtown & the LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsImagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
Museum of Contemporary Photography, South Loop, Downtown & the LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsImagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
The Palette & Chisel Academy of Fine Arts, Downtown, the Loop & West LoopSee paintings and drawings by 32 artists under 40 in Palette & Chisel’s national emerging-artist showcase.
The Palette & Chisel Academy of Fine Arts, Downtown, the Loop & West LoopSee paintings and drawings by 32 artists under 40 in Palette & Chisel’s national emerging-artist showcase.
