#1
Sun, Oct 11, 2026 · 7:00pm
Olivia Rodrigo – The Unraveled Tour
Pilsen, West Town & the West Side
Pop star's arena tour opens its two-night Chicago stand, with Wolf Alice as special guest.
One Weekend Only
Things to Do in Pilsen, West Town & the West Side Columbus Day Weekend 2026
18 picks
The 10 best things to do in Pilsen, West Town & the West Side over Columbus Day Weekend (Oct 9–12)
- Olivia Rodrigo – The Unraveled Tour — Sun, Oct 11 7:00pm · Pilsen
- Chicago Blackhawks vs. Carolina Hurricanes — Sat, Oct 10 6:00pm · Pilsen
- Pre-Season: Chicago Bulls v Memphis Grizzlies — Fri, Oct 9 7:00pm · Pilsen
- Olivia Rodrigo: The Unraveled Tour – Night Two — Monday, October 12, 7:00 PM · Pilsen
- Design at 329 Vintage Clothing Pop-Up — Saturday, October 10 12–6 PM · Pilsen
- Armand Hammer with Quelle Chris and Open Mike Eagle — Saturday, October 10; doors 7:00 PM · Pilsen
- Afrojack Presents: Control — Friday, October 9 Doors 10 PM · Pilsen
- Maddix — Saturday, October 10 Doors 10 PM · Pilsen
- Indigenous Peoples' Day Celebration at Harrison — Saturday, October 10, 11am–4pm · Free · Pilsen
- The Heart of the Story at Douglass — Friday, October 9 6–8 PM · Free · Pilsen
#1Sun, Oct 11, 2026 · 7:00pm · One Weekend Only
Olivia Rodrigo – The Unraveled Tour
Pop star's arena tour opens its two-night Chicago stand, with Wolf Alice as special guest.
Add to calendar#2
Sat, Oct 10, 2026 · 6:00pmPaid ticket required
Chicago Blackhawks vs. Carolina Hurricanes
Pilsen, West Town & the West Side
The Blackhawks host the Carolina Hurricanes for a night of NHL hockey at the United Center.
One Day Only
#2Sat, Oct 10, 2026 · 6:00pm · One Day Only
Chicago Blackhawks vs. Carolina Hurricanes
The Blackhawks host the Carolina Hurricanes for a night of NHL hockey at the United Center.
Add to calendar#3
Fri, Oct 9, 2026 · 7:00pm
Pre-Season: Chicago Bulls v Memphis Grizzlies
Pilsen, West Town & the West Side
The Bulls play the Memphis Grizzlies in an NBA preseason game at the United Center.
One Day Only
#3Fri, Oct 9, 2026 · 7:00pm · One Day Only
Pre-Season: Chicago Bulls v Memphis Grizzlies
The Bulls play the Memphis Grizzlies in an NBA preseason game at the United Center.
Add to calendar#4
United Center, Near West Side, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsMonday, October 12, 2026, 7:00 PMTickets via Ticketmaster
Olivia Rodrigo: The Unraveled Tour – Night Two
Pilsen, West Town & the West Side
Olivia Rodrigo returns to the United Center for night two of the Unraveled Tour.
One Day Only
#4Monday, October 12, 2026, 7:00 PM · One Day Only
United Center, Near West Side, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsOlivia Rodrigo: The Unraveled Tour – Night Two
Olivia Rodrigo returns to the United Center for night two of the Unraveled Tour.
Add to calendar#5
Design at 329, Pilsen, West Town & the West SideAdam Jones, Ph.D. · CC BY-SA 3.0 · Wikimedia CommonsSaturday, October 10, 2026 · 12–6 PMOpen access
Design at 329 Vintage Clothing Pop-Up
Pilsen, West Town & the West Side
Design at 329's dealers open their Pilsen warehouse for a Chicago Fashion Week vintage pop-up.
One Day Only
#5Saturday, October 10, 2026 · 12–6 PM · One Day Only
Design at 329, Pilsen, West Town & the West SideAdam Jones, Ph.D. · CC BY-SA 3.0 · Wikimedia CommonsDesign at 329 Vintage Clothing Pop-Up
Design at 329's dealers open their Pilsen warehouse for a Chicago Fashion Week vintage pop-up.
Add to calendar#6
Thalia Hall, Pilsenvictorgrigas · CC BY-SA 3.0 · Wikimedia CommonsSaturday, October 10, 2026; doors 7:00 PMTicketed
Armand Hammer with Quelle Chris and Open Mike Eagle
Thalia Hall, Pilsen
Three sharp independent hip-hop acts share one bill at Thalia Hall in Pilsen.
One Day Only
#6Saturday, October 10, 2026; doors 7:00 PM · One Day Only
Thalia Hall, Pilsenvictorgrigas · CC BY-SA 3.0 · Wikimedia CommonsArmand Hammer with Quelle Chris and Open Mike Eagle
Three sharp independent hip-hop acts share one bill at Thalia Hall in Pilsen.
Add to calendar#7
Radius Chicago, Near South Side, Pilsen, West Town & the West SideFriday, October 9, 2026 · Doors 10 PMTicketed
Afrojack Presents: Control
Pilsen, West Town & the West Side
Afrojack Presents: Control has enough weekend energy to earn a spot on the board.
Limited Run
#7Friday, October 9, 2026 · Doors 10 PM · Limited Run
Radius Chicago, Near South Side, Pilsen, West Town & the West SideAfrojack Presents: Control
Afrojack Presents: Control has enough weekend energy to earn a spot on the board.
Add to calendar#8
Cermak Hall, East Pilsen, Pilsen, West Town & the West SideSaturday, October 10, 2026 · Doors 10 PMTicketed
Maddix
Pilsen, West Town & the West Side
Maddix brings big-room techno to Cermak Hall in a separate late-night show.
Limited Run
#8Saturday, October 10, 2026 · Doors 10 PM · Limited Run
Cermak Hall, East Pilsen, Pilsen, West Town & the West Side#9
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
#9Saturday, 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#10
Douglass Park, North Lawndale, Pilsen, West Town & the West SideFriday, October 9, 2026 · 6–8 PMFREE
The Heart of the Story at Douglass
Pilsen, West Town & the West Side
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
FreeOne Day Only
#10Friday, October 9, 2026 · 6–8 PM · One Day Only
Douglass Park, North Lawndale, Pilsen, West Town & the West SideThe Heart of the Story at Douglass
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
Add to calendarMore this weekend
#11
Thalia Hall, PilsenSat, Oct 10, 2026 · 11:30am
Rock and Roll Playhouse – The Music of Grateful Dead for Kids
Thalia Hall, Pilsen
Rock and Roll Playhouse – The Music of Grateful Dead for Kids has enough weekend energy to earn a spot on the board.
One Day Only
#11Sat, Oct 10, 2026 · 11:30am · One Day Only
Thalia Hall, PilsenRock and Roll Playhouse – The Music of Grateful Dead for Kids
Rock and Roll Playhouse – The Music of Grateful Dead for Kids has enough weekend energy to earn a spot on the board.
Add to calendar#12
Sun, Oct 11, 2026 · 7:30pm
Emei - Night at the Opera Tour
Pilsen, West Town & the West Side
Emei plays Thalia Hall in Pilsen on the Night at the Opera Tour.
One Day Only
#12Sun, Oct 11, 2026 · 7:30pm · One Day Only
Emei - Night at the Opera Tour
Emei plays Thalia Hall in Pilsen on the Night at the Opera Tour.
Add to calendar#13
Malcolm X College, Near West Side, Pilsen, West Town & the West SideSaturday, October 10, 2026; doors 10:30 AM, programming 11:00 AM–4:00 PMFREE
Healing Arts Chicago Summit
Pilsen, West Town & the West Side
Healing Arts Chicago Summit has enough weekend energy to earn a spot on the board.
FreeLimited Run
#13Saturday, October 10, 2026; doors 10:30 AM, programming 11:00 AM–4:00 PM · Limited Run
Malcolm X College, Near West Side, Pilsen, West Town & the West SideHealing Arts Chicago Summit
Healing Arts Chicago Summit has enough weekend energy to earn a spot on the board.
Add to calendar#14
USG Arena at Blackhawks Ice Center, 1801 W Jackson Blvd, Pilsen, West Town & the West SideSaturday, October 10, 2026 · 3 PMTicketed
Chicago Steel vs. Muskegon Lumberjacks — Ogre Day
Pilsen, West Town & the West Side
The Steel’s second Muskegon game of the weekend celebrates Shrek’s 25th anniversary.
Limited Run
#14Saturday, October 10, 2026 · 3 PM · Limited Run
USG Arena at Blackhawks Ice Center, 1801 W Jackson Blvd, Pilsen, West Town & the West SideChicago Steel vs. Muskegon Lumberjacks — Ogre Day
The Steel’s second Muskegon game of the weekend celebrates Shrek’s 25th anniversary.
Add to calendarThe whole weekend, in one email.
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#15
5 Rabanitos, Pilsen, West Town & the West SideRuns through Oct 4, 2026$105
Street Foods of Pilsen Food Tour
Pilsen, West Town & the West Side
A guided food tour through Pilsen's street food, murals and neighborhood history.
Limited Run
#15Runs through Oct 4, 2026 · Limited Run
5 Rabanitos, Pilsen, West Town & the West SideStreet Foods of Pilsen Food Tour
A guided food tour through Pilsen's street food, murals and neighborhood history.
Add to calendar#16
National Museum of Mexican Art, Pilsen, West Town & the West SideSep 25, 2026–Nov 29, 2026Free
Where Memory Lives:: 40 Years of Día de Muertos
Pilsen, West Town & the West Side
Where Memory Lives:: 40 Years of Día de Muertos is listed for Chicago this weekend.
FreeArt
#16Sep 25, 2026–Nov 29, 2026 · Limited Run
National Museum of Mexican Art, Pilsen, West Town & the West SideWhere Memory Lives:: 40 Years of Día de Muertos
Where Memory Lives:: 40 Years of Día de Muertos is listed for Chicago this weekend.
Add to calendar#17
Intuit Art Museum, Pilsen, West Town & the West SideJun 18, 2026–Jan 31, 2027
Cutting and Pasting a World: The Paper Craft of Henry Darger
Pilsen, West Town & the West Side
Cutting and Pasting a World: The Paper Craft of Henry Darger is listed for Chicago this weekend.
ArtLimited Run
#17Jun 18, 2026–Jan 31, 2027 · Limited Run
Intuit Art Museum, Pilsen, West Town & the West SideCutting and Pasting a World: The Paper Craft of Henry Darger
Cutting and Pasting a World: The Paper Craft of Henry Darger is listed for Chicago this weekend.
Add to calendar#18
National Museum of Mexican Art, Pilsen, West Town & the West SideAug 15, 2026–Feb 7, 2027
Vivir la Tierra: Acquisitions from the Permanent Collection 2010–2026
Pilsen, West Town & the West Side
Vivir la Tierra: Acquisitions from the Permanent Collection 2010–2026 is listed for Chicago this.
ArtLimited Run
#18Aug 15, 2026–Feb 7, 2027 · Limited Run
National Museum of Mexican Art, Pilsen, West Town & the West SideVivir la Tierra: Acquisitions from the Permanent Collection 2010–2026
Vivir la Tierra: Acquisitions from the Permanent Collection 2010–2026 is listed for Chicago this.
Add to calendarAbout this list
Stumblday's hand-checked ranking of the best things to do in Pilsen, West Town & the West Side over Columbus Day weekend 2026 (Oct 10–12): 18 picks.
