#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
Chicago: Weekend of Oct 23–25, 2026
247 picks
The 10 best things to do in Chicago the weekend of Oct 23–25
- 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
- Comedy Hour at Annoyance Theatre — Fri, Oct 23 12:00am · Free · Annoyance Theatre & Bar
- American Prophets: Writers, Religion, and Culture — Fri, Oct 23 10:00am · Downtown
- Topdog/Underdog — Fri, Oct 23 7:30pm · Lincoln Park
- Oktoberfest Nation Chicago — Sep 17–Oct 24; select days · Downtown
- 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
What's free the weekend of Oct 23–25?
- Arts in the Dark Halloween Parade — Sat, Oct 24 6:00pm · Free · Columbus Dr./Balbo Dr.
- Meet Me on Milwaukee (MMoM) — Sun, Oct 25 10:00am · Free · Logan Square
- teamLab: Everything Exists in Infinite Continuity — September 22 – February 21, 2027 · Free · Hyde Park
- “Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire” — Fri, Oct 23 8:00am · Free · Harold Washington Library Center
- We the People: Life, Liberty and the Pursuit of Beauty in Greektown Chicago — Fri, Oct 23 · Free · Downtown
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
Annoyance Theatre & BarFri, Oct 23, 2026 · 12:00amFree
Comedy Hour at Annoyance Theatre
Annoyance Theatre & Bar
Comedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
FreeLimited Run
#5Fri, Oct 23, 2026 · 12:00am · Limited Run
Annoyance Theatre & BarComedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
Add to calendar#6
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
#6Fri, 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#7
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
#7Fri, Oct 23, 2026 · 7:30pm · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & Wrigleyville#8
Oktoberfest Nation – Fulton Market, Fulton Market, Downtown, the Loop & West Loopajay_suresh · CC BY 2.0 · Wikimedia CommonsSep 17–Oct 24, 2026; select days, timed-entry ticketsTicket required for entry
Oktoberfest Nation Chicago
Downtown, the Loop & West Loop
A Fulton Market Oktoberfest with imported Hofbräu beer, carnival rides and stein-holding contests.
Limited Run
#8Sep 17–Oct 24, 2026; select days, timed-entry tickets · Limited Run
Oktoberfest Nation – Fulton Market, Fulton Market, Downtown, the Loop & West Loopajay_suresh · CC BY 2.0 · Wikimedia CommonsOktoberfest Nation Chicago
A Fulton Market Oktoberfest with imported Hofbräu beer, carnival rides and stein-holding contests.
Add to calendar#9
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
#9Fri, 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#10
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
#10Fri, Oct 23, 2026 · 7:00pm · Limited Run
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West LoopNew this week
Just listed, many by the organizers themselves
Garam Masala Comedy Dating Show: Shacking Up in Chicago$19.64–$54.86From the organizer
Arts in the Dark Halloween ParadeFree
¡tinta Ardiente!: Igniting Community Through Collective Action
Threads of a Nation: Preserving Presidential Clothing
Garam Masala Comedy Dating Show: Shacking Up in ChicagoTicketed, price at link
Adam Ray – Chicago – Who Is Me Tour
This Wild Life w/ Nate Bergman
Austin Snell (21+ Event)
More picks for Oct 23–25, 2026
#11
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
#11Sat, 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#12
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
#12Sep 5 – Oct 25, 2026 · Limited Run
Black Ensemble Theater, Uptown#13
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
#13Fri, Oct 23, 2026 · 10:00am · Limited Run
Chicago Children’s Museum, Downtown, the Loop & West Loop#14
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
#14Sat, 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 calendarPlanning ahead for Oct 23–25, 2026?
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#15
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln SquareSat, Oct 24, 2026 · 10:30am
Kino, Kaffee und Kuchen
Andersonville, Uptown & Lincoln Square
Kino, Kaffee und Kuchen at DANK Haus German American Cultural Center.
Limited Run
#15Sat, Oct 24, 2026 · 10:30am · Limited Run
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln SquareKino, Kaffee und Kuchen
Kino, Kaffee und Kuchen at DANK Haus German American Cultural Center.
Add to calendar#16
The Second City, Lincoln Park, Lakeview & WrigleyvilleSat, Oct 24, 2026 · 7:30pm$25
Baby Wants Candy! The Original Completely Improvised Musical
Lincoln Park, Lakeview & Wrigleyville
Baby Wants Candy! The Original Completely Improvised Musical at The Second City.
Limited Run
#16Sat, Oct 24, 2026 · 7:30pm · Limited Run
The Second City, Lincoln Park, Lakeview & WrigleyvilleBaby Wants Candy! The Original Completely Improvised Musical
Baby Wants Candy! The Original Completely Improvised Musical at The Second City.
Add to calendar#17
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
#17Fri, Oct 23, 2026 · Limited Run
NoMI, Downtown, the Loop & West Loop#18
Stars & Garters#18Sat, Oct 24, 2026 · 7:00pm · Limited Run
Stars & Garters#19
Inside Chicago Walking Tours, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 4:00pm
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Downtown, the Loop & West Loop
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour at Inside Chicago Walking.
Limited Run
#19Fri, Oct 23, 2026 · 4:00pm · Limited Run
Inside Chicago Walking Tours, Downtown, the Loop & West LoopHaunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour at Inside Chicago Walking.
Add to calendar#20
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 23, 2026 · 7:30pm
Vladimir
Lincoln Park, Lakeview & Wrigleyville
Vladimir at Theater Wit.
Limited Run
#20Fri, Oct 23, 2026 · 7:30pm · Limited Run
Theater Wit, Lincoln Park, Lakeview & Wrigleyville#21
CinespaceFri, Oct 23, 2026 · 11:00am
Serial Killer: The Exhibition
Cinespace
Serial Killer: The Exhibition at Cinespace.
Limited Run
#21Fri, Oct 23, 2026 · 11:00am · Limited Run
Cinespace#22
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
#22Fri, 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#23
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 7:00pm
Drunk Shakespeare: Drunk Dracula (21+ Event)
Downtown, the Loop & West Loop
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Limited Run
#23Fri, Oct 23, 2026 · 7:00pm · Limited Run
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event)
Drunk Shakespeare: Drunk Dracula (21+ Event) at The Lion Theatre.
Add to calendar#24
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
#24Sun, Oct 25, 2026 · 6:00pm · Limited Run
iO Theater, Lincoln Park, Lakeview & WrigleyvilleAbout this list
Stumblday's hand-checked ranking of the best things to do in Chicago the weekend of Oct 23–25, 2026: 247 picks, refreshed weekly. Concerts, festivals, art, markets, and free outdoor events.