Stumblday's hand-checked ranking of the best things to do in Chicago on Saturday, Sep 26: 35 picks, refreshed weekly.
35 picks · checked Sep 10
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.
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.
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.
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.
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.
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.
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.
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.
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!
Gallagher Way, Lincoln Park, Lakeview & WrigleyvilleNairn McWilliams · CC BY-SA 2.0 · Wikimedia CommonsCompare Chicago wing makers at Gallagher Way, with live music and competitions between bites.
Gallagher Way, Lincoln Park, Lakeview & WrigleyvilleNairn McWilliams · CC BY-SA 2.0 · Wikimedia CommonsCompare Chicago wing makers at Gallagher Way, with live music and competitions between bites.
north-sideLive bands, German food and beer, a keg tap, Kinderfest and a Battle of the Bands round out this Oktoberfest.
north-sideLive bands, German food and beer, a keg tap, Kinderfest and a Battle of the Bands round out this Oktoberfest.
Chicago Athletic Association – The Unbound Collection by Hyatt, Downtown, the Loop & West LoopU.S. Marine Corps photo by Lance Cpl. Steven Wells · Public domain · Wikimedia CommonsChicago Wellness Week links movement, demonstrations and conversations across venues, with a flagship at the Athletic Association.
Chicago Athletic Association – The Unbound Collection by Hyatt, Downtown, the Loop & West LoopU.S. Marine Corps photo by Lance Cpl. Steven Wells · Public domain · Wikimedia CommonsChicago Wellness Week links movement, demonstrations and conversations across venues, with a flagship at the Athletic Association.
1341 W. Randolph Street, Chicago, IL 60607, West Loop, Downtown, the Loop & West LoopJohn W. Taylor · Public domain · Wikimedia CommonsHunt for vintage clothing, vinyl and antiques at Randolph Street Market’s indoor-and-outdoor September edition.
1341 W. Randolph Street, Chicago, IL 60607, West Loop, Downtown, the Loop & West LoopJohn W. Taylor · Public domain · Wikimedia CommonsHunt for vintage clothing, vinyl and antiques at Randolph Street Market’s indoor-and-outdoor September edition.
Participating Andersonville businesses, Andersonville, Uptown & Lincoln SquareZagalejo · Public domain · Wikimedia CommonsFind Chicago artists inside Andersonville shops and neighborhood spaces during a weekend built for browsing and discovery.
Participating Andersonville businesses, Andersonville, Uptown & Lincoln SquareZagalejo · Public domain · Wikimedia CommonsFind Chicago artists inside Andersonville shops and neighborhood spaces during a weekend built for browsing and discovery.
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.
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.
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.
Art Institute of Chicago, Gallery 107, Downtown, the Loop & West LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsRare Edo-period woodblock prints by Utamaro fill Gallery 107.
Art Institute of Chicago, Gallery 107, Downtown, the Loop & West LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsRare Edo-period woodblock prints by Utamaro fill Gallery 107.
Chicago Theater Works, Lincoln Park, Lakeview & WrigleyvilleLoew, Inc. · Public domain · Wikimedia CommonsExplore sustainable fashion through a runway show, designer conversations and a symposium offered in a day-pass bundle.
Chicago Theater Works, Lincoln Park, Lakeview & WrigleyvilleLoew, Inc. · Public domain · Wikimedia CommonsExplore sustainable fashion through a runway show, designer conversations and a symposium offered in a day-pass bundle.
Northwestern Medicine Field, 34W002 Cherry Lane, Far SuburbsThrowback hip-hop shares the field with taco vendors and margaritas at the 21+ Tacos and Tequila Festival in Geneva.
Northwestern Medicine Field, 34W002 Cherry Lane, Far SuburbsThrowback hip-hop shares the field with taco vendors and margaritas at the 21+ Tacos and Tequila Festival in Geneva.
Clark Street between Addison and Newport, Wrigleyville, Lincoln Park, Lakeview & WrigleyvilleKen Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia CommonsClark Street Live brings two stages of country and local bands, neighborhood food and shopping to a new Wrigleyville festival.
Clark Street between Addison and Newport, Wrigleyville, Lincoln Park, Lakeview & WrigleyvilleKen Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia CommonsClark Street Live brings two stages of country and local bands, neighborhood food and shopping to a new Wrigleyville festival.
