#1
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
Free Things to Do in Chicago the Weekend of Oct 23–25, 2026
18 picks
The 10 best free things to do in Chicago the weekend of Oct 23–25
- Fall Fest at Lincoln Park Zoo — Fri, Oct 23 8:00am · Free · Lincoln Park
- 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
- 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
- ART on THE Mart — Thursdays through Sundays, 7:30–8:00 PM · Free · Downtown
- If Emmett Till Lived: Freedom on American Ground — September 10–December 19 · Free · Downtown
Lincoln Park Zoo, Lincoln Park#1Fri, Oct 23, 2026 · 8:00am · Limited Run
Lincoln Park Zoo, Lincoln Park#2
Wicker ParkSun, Oct 25, 2026 · 8:00amFree
Wicker Park Farmers Market
Wicker Park
Wicker Park Farmers Market at Wicker Park.
FreeLimited Run
#2Sun, Oct 25, 2026 · 8:00am · Limited Run
Wicker Park#3
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
#3Fri, 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#4
Columbus Dr./Balbo Dr.Sat, Oct 24, 2026 · 6:00pmFree
Arts in the Dark Halloween Parade
Columbus Dr./Balbo Dr.
Arts in the Dark Halloween Parade at Columbus Dr./Balbo Dr.
FreeOne Day Only
#4Sat, Oct 24, 2026 · 6:00pm · One Day Only
Columbus Dr./Balbo Dr.Arts in the Dark Halloween Parade
Arts in the Dark Halloween Parade at Columbus Dr./Balbo Dr.
Add to calendar#5
Milwaukee Ave from North/Damen to Ashland, Logan Square, Wicker Park & BucktownSun, Oct 25, 2026 · 10:00amFree
Meet Me on Milwaukee (MMoM)
Logan Square, Wicker Park & Bucktown
Meet Me on Milwaukee (MMoM) has enough weekend energy to earn a spot on the board.
FreeLimited Run
#5Sun, Oct 25, 2026 · 10:00am · Limited Run
Milwaukee Ave from North/Damen to Ashland, Logan Square, Wicker Park & BucktownMeet Me on Milwaukee (MMoM)
Meet Me on Milwaukee (MMoM) has enough weekend energy to earn a spot on the board.
Add to calendar#6
Smart Museum of Art, Hyde ParkAdam Jones, Ph.D. · CC BY-SA 3.0 · Wikimedia CommonsSeptember 22, 2026 – February 21, 2027; Tuesday–Sunday 10 a.m.–4:30 p.m.Free
teamLab: Everything Exists in Infinite Continuity
Smart Museum of Art, Hyde Park
The Tokyo art collective teamLab's immersive show at the Smart Museum, with free admission.
FreeArt
#6September 22, 2026 – February 21, 2027; Tuesday–Sunday 10 a.m.–4:30 p.m. · Limited Run
Smart Museum of Art, Hyde ParkAdam Jones, Ph.D. · CC BY-SA 3.0 · Wikimedia CommonsteamLab: Everything Exists in Infinite Continuity
The Tokyo art collective teamLab's immersive show at the Smart Museum, with free admission.
Add to calendar#7
Harold Washington Library CenterFri, Oct 23, 2026 · 8:00amFree
“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire”
Harold Washington Library Center
“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire” at Harold Washington.
FreeArt
#7Fri, Oct 23, 2026 · 8:00am · Limited Run
Harold Washington Library Center“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire”
“Pulitzer on the Road: Prize-Winning Works That Inform, Empower & Inspire” at Harold Washington.
Add to calendar#8
Greektown Chicago, Downtown, the Loop & West LoopFri, Oct 23, 2026Free
We the People: Life, Liberty and the Pursuit of Beauty in Greektown Chicago
Downtown, the Loop & West Loop
We the People: Life, Liberty and the Pursuit of Beauty in Greektown Chicago at Greektown Chicago.
FreeLimited Run
#8Fri, Oct 23, 2026 · Limited Run
Greektown Chicago, Downtown, the Loop & West LoopWe the People: Life, Liberty and the Pursuit of Beauty in Greektown Chicago
We the People: Life, Liberty and the Pursuit of Beauty in Greektown Chicago at Greektown Chicago.
Add to calendar#9
Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West LoopChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia CommonsThursdays through Sundays, 7:30–8:00 PM, through Nov 15, 2026Free and open to the public
ART on THE Mart
Downtown, the Loop & West Loop
ART on THE Mart is listed for Chicago this weekend.
FreeArt
#9Thursdays 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 LoopChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia Commons#10
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
Downtown, the Loop & West Loop
Imagine the life Emmett Till was denied through a free MoCP exhibition drawing on photographs by more than 110 artists.
FreeArt
#10September 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 calendarMore picks for Oct 23–25, 2026
#11
Chicago Cultural Center, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 10:00amFree
Tangible Sound: Arrival to a Higher Ground
Downtown, the Loop & West Loop
Tangible Sound: Arrival to a Higher Ground at Chicago Cultural Center.
FreeLimited Run
#11Fri, Oct 23, 2026 · 10:00am · Limited Run
Chicago Cultural Center, Downtown, the Loop & West LoopTangible Sound: Arrival to a Higher Ground
Tangible Sound: Arrival to a Higher Ground at Chicago Cultural Center.
Add to calendar#12
Chicago Cultural Center, Downtown, the Loop & West LoopFri, Oct 23, 2026 · 1:30pmFREE
Chicago Greeter – Loop InstaGreeter
Downtown, the Loop & West Loop
Chicago Greeter – Loop InstaGreeter at Chicago Cultural Center.
FreeLimited Run
#12Fri, Oct 23, 2026 · 1:30pm · Limited Run
Chicago Cultural Center, Downtown, the Loop & West LoopChicago Greeter – Loop InstaGreeter
Chicago Greeter – Loop InstaGreeter at Chicago Cultural Center.
Add to calendar#13
Stars and Garters TheaterSat, Oct 24, 2026 · 7:00pmFree
FreakShow & Tell
Stars and Garters Theater
FreakShow & Tell at Stars & Garters Theater.
FreeLimited Run
#13Sat, Oct 24, 2026 · 7:00pm · Limited Run
Stars and Garters Theater#14
Lincoln AvenueSat, Oct 24, 2026 · 1:00pmFree
Spooktacular: Lincoln Avenue
Lincoln Avenue
Spooktacular: Lincoln Avenue at Lincoln Avenue.
FreeOne Day Only
#14Sat, Oct 24, 2026 · 1:00pm · One Day Only
Lincoln AvenuePlanning ahead for Oct 23–25, 2026?
It lands the Friday before, plus every Friday until then. Unsubscribe anytime.
#15
Jackson Junge GalleryFri, Oct 23, 2026 · 6:00pmFree
Wicker Park Bucktown’s “First Fridays” Art Walk
Jackson Junge Gallery
Wicker Park Bucktown’s “First Fridays” Art Walk at Jackson Junge Gallery.
FreeLimited Run
#15Fri, Oct 23, 2026 · 6:00pm · Limited Run
Jackson Junge GalleryWicker Park Bucktown’s “First Fridays” Art Walk
Wicker Park Bucktown’s “First Fridays” Art Walk at Jackson Junge Gallery.
Add to calendar#16
100 W. Division St.Sat, Oct 24, 2026 · 7:00amFree
Division Street Farmers Market
100 W. Division St.
Division Street Farmers Market at 100 W. Division St.
FreeLimited Run
#16Sat, Oct 24, 2026 · 7:00am · Limited Run
100 W. Division St.#17
Special Collections Research Center Exhibition GalleryFri, Oct 23, 2026 · 9:00amFree
Created Equal: The Premises and Promises of the Declaration of Independence
Special Collections Research Center Exhibition Gallery
Created Equal: The Premises and Promises of the Declaration of Independence at Special Collections.
FreeArt
#17Fri, Oct 23, 2026 · 9:00am · Limited Run
Special Collections Research Center Exhibition GalleryCreated Equal: The Premises and Promises of the Declaration of Independence
Created Equal: The Premises and Promises of the Declaration of Independence at Special Collections.
Add to calendar#18
Wish FieldSat, Oct 24, 2026 · 2:00pmFree
DePaul Athletics Men’s Soccer
Wish Field
DePaul Athletics Men’s Soccer at Wish Field.
FreeLimited Run
#18Sat, Oct 24, 2026 · 2:00pm · Limited Run
Wish FieldAbout this list
Stumblday's hand-checked ranking of the best free things to do in Chicago the weekend of Oct 23–25, 2026: 18 picks, refreshed weekly.
