#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
Music in Pilsen, Chicago Columbus Day Weekend 2026
8 picks
The 8 best music picks in Pilsen, Chicago over Columbus Day Weekend (Oct 9–12)
- Olivia Rodrigo – The Unraveled Tour — Sun, Oct 11 7:00pm · Pilsen
- Olivia Rodrigo: The Unraveled Tour – Night Two — Monday, October 12, 7:00 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
- Hamdi FC vs. Chicago — Saturday, October 10 Doors 10 PM · Downtown
- Maddix — Saturday, October 10 Doors 10 PM · Pilsen
- Rock and Roll Playhouse – The Music of Grateful Dead for Kids — Sat, Oct 10 11:30am · Pilsen
- Emei - Night at the Opera Tour — Sun, Oct 11 7:30pm · 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
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
#2Monday, 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#3
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
#3Saturday, 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#4
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
#4Friday, 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#5
Radius Chicago, East Pilsen, Downtown, the Loop & West LoopSaturday, October 10, 2026 · Doors 10 PMTicketed
Hamdi FC vs. Chicago
Downtown, the Loop & West Loop
Hamdi’s bass tour lands at Radius with Taiki Nulight and a three-DJ back-to-back set.
Limited Run
#5Saturday, 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#6
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
#6Saturday, October 10, 2026 · Doors 10 PM · Limited Run
Cermak Hall, East Pilsen, Pilsen, West Town & the West Side#7
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
#7Sat, 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#8
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
#8Sun, 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 calendarAbout this list
Stumblday's hand-checked ranking of the best music in Pilsen, Chicago, Pilsen, West Town & the West Side over Columbus Day weekend 2026 (Oct 10–12): 8 picks.
