#1
Sun, Oct 11, 2026 · 7:00pm
Olivia Rodrigo – The Unraveled Tour
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, Chicago the Weekend of Oct 9–12, 2026
Stumblday's hand-checked ranking of the best things to do in Pilsen, Chicago, Pilsen, West Town & the West Side the weekend of Oct 9–12, 2026: 23 picks.
23 picks · checked Sep 21
23 picks
#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 · 6:00pm
Chicago Blackhawks vs. Carolina Hurricanes
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
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
The second of two United Center nights, on the holiday, is the other shot at a top pop act.
Limited Run
#3Monday, October 12, 2026, 7:00 PM · Limited Run
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
The second of two United Center nights, on the holiday, is the other shot at a top pop act.
Add to calendar#4
Fri, Oct 9, 2026 · 7:00pm
Pre-Season: Chicago Bulls v Memphis Grizzlies
The Bulls play the Memphis Grizzlies in an NBA preseason game at the United Center.
Limited Run
#4Fri, Oct 9, 2026 · 7:00pm · Limited Run
Pre-Season: Chicago Bulls v Memphis Grizzlies
The Bulls play the Memphis Grizzlies in an NBA preseason game at the United Center.
Add to calendarPlanning ahead for Oct 9–12, 2026?
It lands the Friday before, plus every Friday until then. Unsubscribe anytime.
#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
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, Pilsen, West Town & the West Sidevictorgrigas · CC BY-SA 3.0 · Wikimedia CommonsSaturday, October 10, 2026; doors 7:00 PMTicketed
Armand Hammer with Quelle Chris and Open Mike Eagle
Three sharp independent hip-hop acts share one bill at Thalia Hall in Pilsen.
Limited Run
#6Saturday, October 10, 2026; doors 7:00 PM · Limited Run
Thalia Hall, Pilsen, West Town & the West Sidevictorgrigas · 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
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
Radius Chicago, East Pilsen, Downtown, the Loop & West LoopSaturday, October 10, 2026 · Doors 10 PMTicketed
Hamdi FC vs. Chicago
Hamdi’s bass tour lands at Radius with Taiki Nulight and a three-DJ back-to-back set.
Limited Run
#8Saturday, October 10, 2026 · Doors 10 PM · Limited Run
Radius Chicago, East Pilsen, Downtown, the Loop & West LoopHamdi FC vs. Chicago
Hamdi’s bass tour lands at Radius with Taiki Nulight and a three-DJ back-to-back set.
Add to calendar#9
Cermak Hall, East Pilsen, Pilsen, West Town & the West SideSaturday, October 10, 2026 · Doors 10 PMTicketed
Maddix
Maddix brings big-room techno to Cermak Hall in a separate late-night show.
Limited Run
#9Saturday, October 10, 2026 · Doors 10 PM · Limited Run
Cermak Hall, East Pilsen, Pilsen, West Town & the West Side#10
Harrison (Carter) Park, Pilsen, West Town & the West SideSaturday, October 10, 2026, 11am–4pmFree
Indigenous Peoples' Day Celebration at Harrison
A free afternoon of music, dance and stories for Indigenous Peoples' Day in Harrison Park.
FreeOne Day Only
#10Saturday, October 10, 2026, 11am–4pm · One Day Only
Harrison (Carter) Park, Pilsen, West Town & the West SideIndigenous Peoples' Day Celebration at Harrison
A free afternoon of music, dance and stories for Indigenous Peoples' Day in Harrison Park.
Add to calendar#11
Douglass Park, North Lawndale, Pilsen, West Town & the West SideFriday, October 9, 2026 · 6–8 PMFREE
The Heart of the Story at Douglass
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
FreeOne Day Only
#11Friday, 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 calendar#12
Thalia Hall, Pilsen, West Town & the West SideSat, Oct 10, 2026 · 11:30am
Rock 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.
One Day Only
#12Sat, Oct 10, 2026 · 11:30am · One Day Only
Thalia Hall, Pilsen, West Town & the West SideRock 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#13
Sun, Oct 11, 2026 · 7:30pm
Emei - Night at the Opera Tour
Emei plays Thalia Hall in Pilsen on the Night at the Opera Tour.
Limited Run
#13Sun, Oct 11, 2026 · 7:30pm · Limited Run
Emei - Night at the Opera Tour
Emei plays Thalia Hall in Pilsen on the Night at the Opera Tour.
Add to calendar#14
Theatre Y, Pilsen, West Town & the West SideSeptember 24–November 1, 2026; Thu–Sat 7 p.m., Sun 5 p.m.FREE
I am the Wind
Theatre Y stages Nobel laureate Jon Fosse's two-hander I Am the Wind.
Limited Run
#14September 24–November 1, 2026; Thu–Sat 7 p.m., Sun 5 p.m. · Limited Run
Theatre Y, Pilsen, West Town & the West Side#15
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
Healing Arts Chicago Summit has enough weekend energy to earn a spot on the board.
FreeLimited Run
#15Saturday, 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#16
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
The Steel’s second Muskegon game of the weekend celebrates Shrek’s 25th anniversary.
Limited Run
#16Saturday, 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 calendar#17
5 Rabanitos, Pilsen, West Town & the West SideSun, Oct 11, 2026 · 1:00pm$105
Street Foods of Pilsen Food Tour
A guided food tour through Pilsen's street food, murals and neighborhood history.
One Day Only
#17Sun, Oct 11, 2026 · 1:00pm · One Day Only
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#18
Taan, Humboldt Park, Pilsen, West Town & the West SideOpen this weekend — recently opened
Taan
A former pop-up's new permanent Humboldt Park home, serving tiger prawns in chu chee curry.
Limited Run
#18Open this weekend — recently opened · Limited Run
Taan, Humboldt Park, Pilsen, West Town & the West SideTaan
A former pop-up's new permanent Humboldt Park home, serving tiger prawns in chu chee curry.
Add to calendar#19
Cinespace, Pilsen, West Town & the West SideWednesdays through Sundays, open since Sep 5, 2026; no end date announced
Serial Killer: The Exhibition
Serial Killer: The Exhibition has enough weekend energy to earn a spot on the board.
ArtLimited Run
#19Wednesdays through Sundays, open since Sep 5, 2026; no end date announced · Limited Run
Cinespace, Pilsen, West Town & the West SideSerial Killer: The Exhibition
Serial Killer: The Exhibition has enough weekend energy to earn a spot on the board.
Add to calendar#20
National Museum of Mexican Art, Pilsen, West Town & the West SideOn view through Nov 29, 2026Free admission
Where Memory Lives: 40 Years of Día de Muertos
Where Memory Lives: 40 Years of Día de Muertos has enough weekend energy to earn a spot on the board.
FreeArt
#20On view through 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 has enough weekend energy to earn a spot on the board.
Add to calendar#21
Ciclo Urbano, Lincoln Park, Pilsen, West Town & the West SideSat, Oct 10, 2026 · 10:00am$25 ($22.50 for members)
Walking Tour: Paseo Boricua and Humboldt Park
Walking Tour: Paseo Boricua and Humboldt Park has enough weekend energy to earn a spot on the board.
One Day Only
#21Sat, Oct 10, 2026 · 10:00am · One Day Only
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#22
Intuit Art Museum, Pilsen, West Town & the West SideOn view through Jan 31, 2027
Cutting and Pasting a World: The Paper Craft of Henry Darger
Cutting and Pasting a World: The Paper Craft of Henry Darger has enough weekend energy to earn a spot on the board.
ArtLimited Run
#22On view through 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 has enough weekend energy to earn a spot on the board.
Add to calendar#23
National Museum of Mexican Art, Pilsen, West Town & the West SideOn view through Feb 7, 2027Free admission
Vivir la Tierra: Acquisitions from the Permanent Collection 2010–2026
Vivir la Tierra: Acquisitions from the Permanent Collection 2010–2026 has enough weekend energy to earn a spot on the board.
FreeArt
#23On view through 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 has enough weekend energy to earn a spot on the board.
Add to calendar