#1
Brookfield Zoo ChicagoFri, Oct 23, 2026 · 10:00am
BOO! at the Zoo
Brookfield Zoo Chicago
BOO! at the Zoo at Brookfield Zoo Chicago.
Limited Run
Things to Do in Chicago on Sunday, Oct 25
137 picks
The 10 best things to do in Chicago on Sunday, Oct 25
- BOO! at the Zoo — Fri, Oct 23 10:00am · Brookfield Zoo Chicago
- Fall Fest at Lincoln Park Zoo — Fri, Oct 23 8:00am · Free · Lincoln Park
- Kowalski — September 15 – October 25 · Downtown
- Wicker Park Farmers Market — Sun, Oct 25 8:00am · Free · Wicker Park
- American Prophets: Writers, Religion, and Culture — Fri, Oct 23 10:00am · Downtown
- Topdog/Underdog — Fri, Oct 23 7:30pm · Lincoln Park
- The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues — Fri, Oct 23 7:00pm · $25 · Facility Theatre
- Jekyll& Hyde — Fri, Oct 23 7:00pm · Downtown
- Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago — Sat, Oct 24 11:00am
- You Can't Fake the Funk — Sep 5 – Oct 25 · Uptown
Brookfield Zoo Chicago#1Fri, Oct 23, 2026 · 10:00am · Limited Run
Brookfield Zoo Chicago#2
Lincoln Park Zoo, Lincoln ParkFri, Oct 23, 2026 · 8:00amFree
Fall Fest at Lincoln Park Zoo
Lincoln Park Zoo, Lincoln Park
Fall Fest at Lincoln Park Zoo at Lincoln Park Zoo.
FreeLimited Run
#2Fri, Oct 23, 2026 · 8:00am · Limited Run
Lincoln Park Zoo, Lincoln Park#3
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsSeptember 15 – October 25, 2026Ticketed via Lookingglass The…
Kowalski
Downtown, the Loop & West Loop
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Limited Run
#3September 15 – October 25, 2026 · Limited Run
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsKowalski
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Add to calendar#4
Wicker ParkSun, Oct 25, 2026 · 8:00amFree
Wicker Park Farmers Market
Wicker Park
Wicker Park Farmers Market at Wicker Park.
FreeLimited Run
#4Sun, Oct 25, 2026 · 8:00am · Limited Run
Wicker Park#5
American Writers Museum, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 10:00am
American Prophets: Writers, Religion, and Culture
Downtown, the Loop & West Loop
American Prophets: Writers, Religion and Culture at American Writers Museum.
ArtLimited Run
#5Fri, Oct 23, 2026 · 10:00am · Limited Run
American Writers Museum, Downtown, the Loop & West LoopAmerican Prophets: Writers, Religion, and Culture
American Prophets: Writers, Religion and Culture at American Writers Museum.
Add to calendar#6
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 23, 2026 · 7:30pm
Topdog/Underdog
Lincoln Park, Lakeview & Wrigleyville
Topdog/Underdog at Steppenwolf Downstairs Theater.
Limited Run
#6Fri, Oct 23, 2026 · 7:30pm · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & Wrigleyville#7
Facility TheatreFri, Oct 23, 2026 · 7:00pm$25
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues
Facility Theatre
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago.
Limited Run
#7Fri, Oct 23, 2026 · 7:00pm · Limited Run
Facility TheatreThe 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago.
Add to calendar#8
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 7:00pm
Jekyll& Hyde
Downtown, the Loop & West Loop
Jekyll& Hyde at Broadway Playhouse at Water Tower Place.
Limited Run
#8Fri, Oct 23, 2026 · 7:00pm · Limited Run
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loop#9
The Ritz-Carlton, Chicago 160 E Pearson St 12th Floor Chicago, IL 60611Sat, Oct 24, 2026 · 11:00am
Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago
Chicago 160 E Pearson St 12th Floor Chicago, IL 60611
Before Midnight – A Cinderella Tea Experience at The Ritz-Carlton, Chicago at The Ritz-Carlton.
Limited Run
#9Sat, Oct 24, 2026 · 11:00am · 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 at The Ritz-Carlton.
Add to calendar#10
Black Ensemble Theater, UptownSep 5 – Oct 25, 2026Ticketed via Black Ensemble T…
You Can't Fake the Funk
Black Ensemble Theater, Uptown
You Can't Fake the Funk is listed for Chicago this weekend.
Limited Run
#10Sep 5 – Oct 25, 2026 · Limited Run
Black Ensemble Theater, UptownMore on Sunday
#11
Chicago Children’s Museum, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 10:00am
Mini Zoom Room
Downtown, the Loop & West Loop
Mini Zoom Room at Chicago Children’s Museum.
ArtLimited Run
#11Fri, Oct 23, 2026 · 10:00am · Limited Run
Chicago Children’s Museum, Downtown, the Loop & West Loop#12
Greenhouse Theater CenterSat, Oct 24, 2026 · 11:00am
If You Give a Mouse a Cookie
Greenhouse Theater Center
If You Give a Mouse a Cookie at Greenhouse Theater Center.
Limited Run
#12Sat, Oct 24, 2026 · 11:00am · Limited Run
Greenhouse Theater CenterIf You Give a Mouse a Cookie
If You Give a Mouse a Cookie at Greenhouse Theater Center.
Add to calendar#13
NoMI, Downtown, the Loop & West LoopFri, Oct 23, 2026
NoMI Gallery
Downtown, the Loop & West Loop
NoMI Gallery | Everything is Bright. All Things are Beautiful. at NoMI.
ArtLimited Run
#13Fri, Oct 23, 2026 · Limited Run
NoMI, Downtown, the Loop & West Loop#14
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 23, 2026 · 7:30pm
Vladimir
Lincoln Park, Lakeview & Wrigleyville
Vladimir at Theater Wit.
Limited Run
#14Fri, Oct 23, 2026 · 7:30pm · Limited Run
Theater Wit, Lincoln Park, Lakeview & WrigleyvillePlanning ahead for Oct 23–25, 2026?
It lands the Friday before, plus every Friday until then. Unsubscribe anytime.
#15
CinespaceFri, Oct 23, 2026 · 11:00am
Serial Killer: The Exhibition
Cinespace
Serial Killer: The Exhibition at Cinespace.
Limited Run
#15Fri, Oct 23, 2026 · 11:00am · Limited Run
Cinespace#16
The Den Theatre, 1331 N Milwaukee Ave, Logan Square, Wicker Park & BucktownFri, Oct 23, 2026 · 7:30pm$12 – $40
Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire”
Logan Square, Wicker Park & Bucktown
Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire” at The Den Theatre.
Limited Run
#16Fri, Oct 23, 2026 · 7:30pm · Limited Run
The Den Theatre, 1331 N Milwaukee Ave, Logan Square, Wicker Park & BucktownRefracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire”
Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire” at The Den Theatre.
Add to calendar#17
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSun, Oct 25, 2026 · 6:00pm$15
Marquee: Musical Improv
Lincoln Park, Lakeview & Wrigleyville
Marquee: Musical Improv at iO Theater.
Limited Run
#17Sun, Oct 25, 2026 · 6:00pm · Limited Run
iO Theater, Lincoln Park, Lakeview & Wrigleyville#18
Redtwist TheatreFri, Oct 23, 2026 · 7:30pm$50
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle”
Redtwist Theatre
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” at Redtwist Theatre.
Limited Run
#18Fri, Oct 23, 2026 · 7:30pm · 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” at Redtwist Theatre.
Add to calendar#19
Chicago’s First Lady CruisesFri, Oct 23, 2026$50
Chicago By Night River & Lake
Chicago’s First Lady Cruises
Chicago By Night River & Lake at Chicago’s First Lady Cruises.
Limited Run
#19Fri, Oct 23, 2026 · Limited Run
Chicago’s First Lady CruisesChicago By Night River & Lake
Chicago By Night River & Lake at Chicago’s First Lady Cruises.
Add to calendar#20
Oil Lamp TheaterFri, Oct 23, 2026 · 7:30pm$55
Oil Lamp Theater Presents “Dial M for Murder”
Oil Lamp Theater
Oil Lamp Theater Presents “Dial M for Murder” at Oil Lamp Theater.
Limited Run
#20Fri, Oct 23, 2026 · 7:30pm · Limited Run
Oil Lamp TheaterOil Lamp Theater Presents “Dial M for Murder”
Oil Lamp Theater Presents “Dial M for Murder” at Oil Lamp Theater.
Add to calendar#21
Theatre Y#21Fri, Oct 23, 2026 · 7:00pm · Limited Run
Theatre Y#22
Malarkey ComedySun, Oct 25, 2026 · 6:00pm$10
Malarkey Comedy Expo League
Malarkey Comedy
Malarkey Comedy Expo League at Malarkey Comedy.
Limited Run
#22Sun, Oct 25, 2026 · 6:00pm · Limited Run
Malarkey Comedy#23
Northlight Theatre, EvanstonSeptember 9 – October 25, 2026 (extended)Ticketed
The Front Page
Northlight Theatre, Evanston
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Limited Run
#23September 9 – October 25, 2026 (extended) · Limited Run
Northlight Theatre, EvanstonThe Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Add to calendar#24
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopFri, Oct 23, 2026
Theater of the Mind
Downtown, the Loop & West Loop
Theater of the Mind at Reid Murdoch Building – 333 N LaSalle.
Limited Run
#24Fri, Oct 23, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopAbout this list
Stumblday's hand-checked ranking of the best things to do in Chicago on Sunday, Oct 25: 137 picks, refreshed weekly.
