#1
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleSep 25, 2026–Oct 18, 2026Free
Fall Fest at Lincoln Park Zoo
Lincoln Park, Lakeview & Wrigleyville
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
FreeLimited Run
Outdoors in Chicago on Saturday, Columbus Day Weekend 2026
18 picks
The 10 best outdoor picks in Chicago on Saturday, Oct 10
- Fall Fest at Lincoln Park Zoo — Sep 25–Oct 18, 2026 · Free · Lincoln Park
- Lincoln Park Wine Fest — October 9–11; Friday 5–10pm · General admission from $30 · Lincoln Park
- Night of 1,000 Jack-o'-Lanterns — October 7–11, 14–18 and 21–25, 6:30–10:30 PM · Adults from $24 for nonmember… · Glencoe
- Longer Than the Sky: Art of the Obama Years — On view July 10 – October 11 · Hyde Park
- Play On! — Chicago Shakespeare Theater — September 11–October 18; selected performances · Downtown
- Abbott Chicago 5K — Saturday, October 10, 7:30 AM start · The Loop
- TenderFest @ East End Plaza at Navy Pier — Sat, Oct 10 12:00pm · Downtown
- Indigenous Peoples' Day Celebration at Harrison — Saturday, October 10, 11am–4pm · Free · Pilsen
- Failure (18 and Over) — Sat, Oct 10 8:00pm · Lincoln Park
- Really Really Free Market — Sat, Oct 10 10:00am · Free · Lincoln Park
Lincoln Park Zoo, Lincoln Park, Lakeview & Wrigleyville#1Sep 25, 2026–Oct 18, 2026 · Limited Run
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleFall Fest at Lincoln Park Zoo
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
Add to calendar#2
Jonquil Park, Lincoln ParkWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsOctober 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pmGeneral admission from $30
Lincoln Park Wine Fest
Jonquil Park, Lincoln Park
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
One Weekend Only
#2October 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pm · One Weekend Only
Jonquil Park, Lincoln ParkWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsLincoln Park Wine Fest
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
Add to calendar#3
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsOctober 7–11, 14–18 and 21–25, 2026, 6:30–10:30 PMAdults from $24 for nonmember…
Night of 1,000 Jack-o'-Lanterns
Glencoe, Far Suburbs
Seventy-five giant pumpkins, live carving and performers light a three-night garden walk.
One Weekend Only
#3October 7–11, 14–18 and 21–25, 2026, 6:30–10:30 PM · One Weekend Only
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsNight of 1,000 Jack-o'-Lanterns
Seventy-five giant pumpkins, live carving and performers light a three-night garden walk.
Add to calendar#4
Logan Center for the Arts, Hyde ParkCharter6281 · CC BY-SA 4.0 · Wikimedia CommonsOn view July 10 – October 11, 2026
Longer Than the Sky: Art of the Obama Years
Logan Center for the Arts, Hyde Park
A curator-led 11 a.m. walkthrough adds a timed hook to this Obama-era art survey.
ArtLimited Run
#4On view July 10 – October 11, 2026 · Limited Run
Logan Center for the Arts, Hyde ParkCharter6281 · CC BY-SA 4.0 · Wikimedia CommonsLonger Than the Sky: Art of the Obama Years
A curator-led 11 a.m. walkthrough adds a timed hook to this Obama-era art survey.
Add to calendar#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
Downtown, the Loop & West Loop
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
Grant Park, The LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsSaturday, October 10, 2026, 7:30 AM start
Abbott Chicago 5K
Grant Park, The Loop
The official 5K sends marathon-weekend runners through a downtown course.
One Day Only
#6Saturday, October 10, 2026, 7:30 AM start · One Day Only
Grant Park, The LoopDiego Delso · CC BY-SA 3.0 · Wikimedia CommonsAbbott Chicago 5K
The official 5K sends marathon-weekend runners through a downtown course.
Add to calendar#7
Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West LoopSat, Oct 10, 2026 · 12:00pm
TenderFest @ East End Plaza at Navy Pier
Downtown, the Loop & West Loop
TenderFest @ East End Plaza at Navy Pier
One Day Only
#7Sat, Oct 10, 2026 · 12:00pm · One Day Only
Navy Pier, 600 E. Grand Ave., Downtown, the Loop & West Loop#8
Harrison (Carter) Park, PilsenSaturday, October 10, 2026, 11am–4pmFree
Indigenous Peoples' Day Celebration at Harrison
Harrison (Carter) Park, Pilsen
A free afternoon of music, dance and stories for Indigenous Peoples' Day in Harrison Park.
FreeOne Day Only
#8Saturday, October 10, 2026, 11am–4pm · One Day Only
Harrison (Carter) Park, PilsenIndigenous Peoples' Day Celebration at Harrison
A free afternoon of music, dance and stories for Indigenous Peoples' Day in Harrison Park.
Add to calendar#9
Sat, Oct 10, 2026 · 8:00pm
Failure (18 and Over)
Lincoln Park, Lakeview & Wrigleyville
Failure plays an 18-and-over show at Park West.
One Day Only
#9Sat, Oct 10, 2026 · 8:00pm · One Day Only
#10
AIDS Garden Chicago, Lincoln Park, Lakeview & WrigleyvilleSat, Oct 10, 2026 · 10:00amFree
Really Really Free Market
Lincoln Park, Lakeview & Wrigleyville
Really Really Free Market has enough weekend energy to earn a spot on the board.
FreeOne Day Only
#10Sat, Oct 10, 2026 · 10:00am · One Day Only
AIDS Garden Chicago, Lincoln Park, Lakeview & WrigleyvilleReally Really Free Market
Really Really Free Market has enough weekend energy to earn a spot on the board.
Add to calendarMore on Saturday
#11
Taan, Humboldt Park, Pilsen, West Town & the West SideOpen this weekend — recently opened
Taan
Pilsen, West Town & the West Side
Taan is listed for Chicago this weekend.
Limited Run
#11Open this weekend — recently opened · Limited Run
Taan, Humboldt Park, Pilsen, West Town & the West Side#12
DuSable Black History Museum and Education Center, Washington Park, Hyde Park, Bronzeville & the South SideSaturday, October 10, 2026, 10:30 AM–12:00 PM
Five Bands Brotherhood Forum Series: The Discipline of a Strong Man
Hyde Park, Bronzeville & the South Side
Five Bands Brotherhood Forum Series: The Discipline of a Strong Man has enough weekend energy to earn a spot on the board.
Limited Run
#12Saturday, October 10, 2026, 10:30 AM–12:00 PM · Limited Run
DuSable Black History Museum and Education Center, Washington Park, Hyde Park, Bronzeville & the South SideFive Bands Brotherhood Forum Series: The Discipline of a Strong Man
Five Bands Brotherhood Forum Series: The Discipline of a Strong Man has enough weekend energy to earn a spot on the board.
Add to calendar#13
Antepli Mediterranean Grill, Albany Park, Andersonville, Uptown & Lincoln SquareOpen this weekend — recently opened
Antepli Mediterranean Grill
Andersonville, Uptown & Lincoln Square
Antepli Mediterranean Grill is listed for Chicago this weekend.
Limited Run
#13Open this weekend — recently opened · Limited Run
Antepli Mediterranean Grill, Albany Park, Andersonville, Uptown & Lincoln SquareAntepli Mediterranean Grill
Antepli Mediterranean Grill is listed for Chicago this weekend.
Add to calendar#14
Wicker ParkSep 20, 2026–Oct 18, 2026
Wicker Park Farmers Market
Wicker Park
Wicker Park Farmers Market is listed for Chicago this weekend.
Limited Run
#14Sep 20, 2026–Oct 18, 2026 · Limited Run
Wicker ParkWicker Park Farmers Market
Wicker Park Farmers Market is listed for Chicago this weekend.
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#15
Wrightwood 659, Lincoln ParkSeptember 25–December 19, 2026; open Fridays and Saturdays with timed-entry tickets$20 general admission
Inner Worlds: Visions from the Hirshhorn Collection
Wrightwood 659, Lincoln Park
Kusama joins Bauermeister and de Saint Phalle in a Hirshhorn Collection exhibition.
ArtLimited Run
#15September 25–December 19, 2026; open Fridays and Saturdays with timed-entry tickets · Limited Run
Wrightwood 659, Lincoln ParkInner Worlds: Visions from the Hirshhorn Collection
Kusama joins Bauermeister and de Saint Phalle in a Hirshhorn Collection exhibition.
Add to calendar#16
Ciclo Urbano, Lincoln Park, Pilsen, West Town & the West SideRuns through Oct 10, 2026$25 ($22.50 for members)
Walking Tour: Paseo Boricua and Humboldt Park
Pilsen, West Town & the West Side
Walking Tour: Paseo Boricua and Humboldt Park has enough weekend energy to earn a spot on the board.
Limited Run
#16Runs through Oct 10, 2026 · Limited Run
Ciclo Urbano, Lincoln Park, Pilsen, West Town & the West SideWalking Tour: Paseo Boricua and Humboldt Park
Walking Tour: Paseo Boricua and Humboldt Park has enough weekend energy to earn a spot on the board.
Add to calendar#17
Green City Market Lincoln Park, Lincoln ParkWednesdays and Saturdays, 7am–1pm, through Nov 21, 2026
Green City Market Lincoln Park
Green City Market Lincoln Park, Lincoln Park
Green City Market Lincoln Park has enough weekend energy to earn a spot on the board.
Limited Run
#17Wednesdays and Saturdays, 7am–1pm, through Nov 21, 2026 · Limited Run
Green City Market Lincoln Park, Lincoln ParkGreen City Market Lincoln Park
Green City Market Lincoln Park has enough weekend energy to earn a spot on the board.
Add to calendar#18
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
#18September 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 calendarAbout this list
Stumblday's hand-checked ranking of the best outdoors in Chicago on Saturday of Columbus Day weekend, Oct 10: 18 picks, refreshed weekly.
