#1
More than 200 sites across Chicago, Downtown, the Loop & West LoopSat–Sun, Oct 17–18Free public festival
Open House Chicago 2026
Open House Chicago 2026 is listed for Chicago this weekend.
FreeOne Weekend Only
Chicago: Weekend of Oct 16–18, 2026
Hand-picked every week — checked against organizers’ own pages.
Stumblday's hand-checked ranking of the best things to do in Chicago the weekend of Oct 16–18, 2026: 240 picks, refreshed weekly. Concerts, festivals, art, markets, and free outdoor events.
240 picks · checked Sep 28
240 picks
The 10 picks
More than 200 sites across Chicago, Downtown, the Loop & West Loop#1Sat–Sun, Oct 17–18 · One Weekend Only
More than 200 sites across Chicago, Downtown, the Loop & West Loop#2
Multiple LocationsOct 16, 2026–Oct 18, 2026
62nd Chicago International Film Festival
62nd Chicago International Film Festival is listed for Chicago this weekend.
One Weekend Only
#2Oct 16, 2026–Oct 18, 2026 · One Weekend Only
Multiple Locations62nd Chicago International Film Festival
62nd Chicago International Film Festival is listed for Chicago this weekend.
Add to calendar#3
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsSep 25, 2026–Oct 18, 2026Free
Fall Fest at Lincoln Park Zoo
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
FreeLimited Run
#3Sep 25, 2026–Oct 18, 2026 · Limited Run
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsFall Fest at Lincoln Park Zoo
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
Add to calendar#4
Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West LoopThursdays through Sundays, 7:30–8:00 PM, through Nov 15, 2026Free and open to the public
ART on THE Mart
ART on THE Mart is listed for Chicago this weekend.
FreeArt
#4Thursdays through Sundays, 7:30–8:00 PM, through Nov 15, 2026 · Limited Run
Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West Loop#5
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Limited Run
#5September 11–October 18, 2026; selected performances · Limited Run
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopPlay On! — Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Add to calendar#6
Museum of Contemporary Photography, South Loop, Downtown, the Loop & West LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsSeptember 10–December 19, 2026; Mon–Wed and Fri–Sat 10 a.m.–5 p.m., Thu 10 a.m.–8 p.m.; Sun closedFree
If Emmett Till Lived: Freedom on American Ground
Imagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
FreeArt
#6September 10–December 19, 2026; Mon–Wed and Fri–Sat 10 a.m.–5 p.m., Thu 10 a.m.–8 p.m.; Sun closed · Limited Run
Museum of Contemporary Photography, South Loop, Downtown, the Loop & West LoopViselippi · CC BY-SA 4.0 · Wikimedia CommonsIf Emmett Till Lived: Freedom on American Ground
Imagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
Add to calendar#7
Music Box Theatre, LakeviewOctober 1–31, 2026; horror screenings most nights, plus a 24-hour marathon on October 24Most screenings $13 ($10 Musi…
Music Box of Horrors: The Final Chapter
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
Limited Run
#7October 1–31, 2026; horror screenings most nights, plus a 24-hour marathon on October 24 · Limited Run
Music Box Theatre, LakeviewMusic Box of Horrors: The Final Chapter
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
Add to calendar#8
Heritage Museum of Asian Art, Hyde Park, Bronzeville & the South SideSep 18, 2026–Oct 16, 2026Free
3rd Fridays Free Admission Museum Night
3rd Fridays Free Admission Museum Night is listed for Chicago this weekend.
FreeArt
#8Sep 18, 2026–Oct 16, 2026 · Limited Run
Heritage Museum of Asian Art, Hyde Park, Bronzeville & the South Side3rd Fridays Free Admission Museum Night
3rd Fridays Free Admission Museum Night is listed for Chicago this weekend.
Add to calendar#9
Antepli Mediterranean Grill, Albany Park, Andersonville, Uptown & Lincoln SquareNick Number · CC BY 4.0 · Wikimedia CommonsOpen this weekend — recently opened
Antepli Mediterranean Grill
Antepli Mediterranean Grill is listed for Chicago this weekend.
Limited Run
#9Open this weekend — recently opened · Limited Run
Antepli Mediterranean Grill, Albany Park, Andersonville, Uptown & Lincoln SquareNick Number · CC BY 4.0 · Wikimedia CommonsAntepli Mediterranean Grill
Antepli Mediterranean Grill is listed for Chicago this weekend.
Add to calendar#10
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsAugust 19–October 18, 2026Tickets via Drury Lane box of…
The Buddy Holly Story
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Limited Run
#10August 19–October 18, 2026 · Limited Run
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsThe Buddy Holly Story
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Add to calendarMore picks for Oct 16–18, 2026
#11
NoMI, Downtown, the Loop & West Loop#11Sep 11, 2026–Oct 18, 2026 · Limited Run
NoMI, Downtown, the Loop & West Loop#12
The Annoyance TheatreSep 18, 2026–Oct 16, 2026$15
Missed Call Sketch Comedy Show
Missed Call Sketch Comedy Show is listed for Chicago this weekend.
Limited Run
#12Sep 18, 2026–Oct 16, 2026 · Limited Run
The Annoyance TheatreMissed Call Sketch Comedy Show
Missed Call Sketch Comedy Show is listed for Chicago this weekend.
Add to calendar#13
The Ritz-Carlton, Chicago 160 E Pearson St 12th Floor Chicago, IL 60611Sep 19, 2026–Oct 18, 2026
Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago
Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago is listed for Chicago.
Limited Run
#13Sep 19, 2026–Oct 18, 2026 · Limited Run
The Ritz-Carlton, Chicago 160 E Pearson St 12th Floor Chicago, IL 60611Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago
Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago is listed for Chicago.
Add to calendar#14
Redtwist TheatreSep 17, 2026–Oct 18, 2026$50
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle”
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” is listed for.
Limited Run
#14Sep 17, 2026–Oct 18, 2026 · Limited Run
Redtwist TheatreRedtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle”
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” is listed for.
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#15
House of Blues Chicago, River North, Downtown, the Loop & West LoopSep 13, 2026–Oct 18, 2026
World Famous Gospel Brunch at House of Blues (CHI)
World Famous Gospel Brunch at House of Blues (CHI) is listed for Chicago this weekend.
Limited Run
#15Sep 13, 2026–Oct 18, 2026 · Limited Run
House of Blues Chicago, River North, Downtown, the Loop & West LoopWorld Famous Gospel Brunch at House of Blues (CHI)
World Famous Gospel Brunch at House of Blues (CHI) is listed for Chicago this weekend.
Add to calendar#16
CinespaceSep 18, 2026–Oct 18, 2026
Serial Killer: The Exhibition
Serial Killer: The Exhibition is listed for Chicago this weekend.
ArtLimited Run
#16Sep 18, 2026–Oct 18, 2026 · Limited Run
CinespaceSerial Killer: The Exhibition
Serial Killer: The Exhibition is listed for Chicago this weekend.
Add to calendar#17
Judy’s Beat Lounge at the Second City Training CenterSep 19, 2026–Oct 17, 2026$25
Standup Throw Down: Millennials vs Gen X
Standup Throw Down: Millennials vs Gen X is listed for Chicago this weekend.
Limited Run
#17Sep 19, 2026–Oct 17, 2026 · Limited Run
Judy’s Beat Lounge at the Second City Training CenterStandup Throw Down: Millennials vs Gen X
Standup Throw Down: Millennials vs Gen X is listed for Chicago this weekend.
Add to calendar#18
Greenhouse Theater CenterSep 26, 2026–Oct 18, 2026
If You Give a Mouse a Cookie
If You Give a Mouse a Cookie is listed for Chicago this weekend.
Limited Run
#18Sep 26, 2026–Oct 18, 2026 · Limited Run
Greenhouse Theater CenterIf You Give a Mouse a Cookie
If You Give a Mouse a Cookie is listed for Chicago this weekend.
Add to calendar#19
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln SquareSep 19, 2026–Oct 17, 2026
Kino, Kaffee und Kuchen
Kino, Kaffee und Kuchen is listed for Chicago this weekend.
Limited Run
#19Sep 19, 2026–Oct 17, 2026 · Limited Run
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln Square#20
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026
Theater of the Mind
Theater of the Mind is listed for Chicago this weekend.
Limited Run
#20Sep 18, 2026–Oct 18, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#21
Annoyance Theatre & BarSep 18, 2026–Oct 17, 2026Free
Comedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre is listed for Chicago this weekend.
FreeLimited Run
#21Sep 18, 2026–Oct 17, 2026 · Limited Run
Annoyance Theatre & BarComedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre is listed for Chicago this weekend.
Add to calendar#22
Open Space ArtsSep 25, 2026–Oct 18, 2026$30.00
The Swallow
The Swallow is listed for Chicago this weekend.
Limited Run
#22Sep 25, 2026–Oct 18, 2026 · Limited Run
Open Space Arts#23
American Writers Museum, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026
American Prophets: Writers, Religion, and Culture
American Prophets: Writers, Religion and Culture is listed for Chicago this weekend.
ArtLimited Run
#23Sep 18, 2026–Oct 18, 2026 · Limited Run
American Writers Museum, Downtown, the Loop & West LoopAmerican Prophets: Writers, Religion, and Culture
American Prophets: Writers, Religion and Culture is listed for Chicago this weekend.
Add to calendar#24
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USASep 18, 2026–Oct 16, 2026$15
Voila: The Improvised Musical
Voila: The Improvised Musical is listed for Chicago this weekend.
Limited Run
#24Sep 18, 2026–Oct 16, 2026 · Limited Run
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USAVoila: The Improvised Musical
Voila: The Improvised Musical is listed for Chicago this weekend.
Add to calendar