#1
Saturday, October 3 and Sunday, October 4, 2026, 8:30pm
The Chicks: Taking the Long Way
The Chicks headline The Auditorium downtown for a single night.
One Weekend Only
Music in West Loop, Chicago the Weekend of Oct 2–4, 2026
Stumblday's hand-checked ranking of the best music in West Loop, Chicago, Downtown, the Loop & West Loop the weekend of Oct 2–4, 2026: 15 picks.
15 picks · checked Sep 21
15 picks
#1Saturday, October 3 and Sunday, October 4, 2026, 8:30pm · One Weekend Only
The Chicks: Taking the Long Way
The Chicks headline The Auditorium downtown for a single night.
Add to calendar#2
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsThrough Oct 4, 2026; Thursday and Saturday at 7:30pm, Friday at 1:30pm, Sunday at 3pmFrom $55
Mäkelä Conducts Mahler 9
Mäkelä leads the orchestra through Mahler's Ninth at Orchestra Hall.
One Weekend Only
#2Through Oct 4, 2026; Thursday and Saturday at 7:30pm, Friday at 1:30pm, Sunday at 3pm · One Weekend Only
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsMäkelä Conducts Mahler 9
Mäkelä leads the orchestra through Mahler's Ninth at Orchestra Hall.
Add to calendar#3
Huntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopSat, Oct 3, 2026 · 8:00pm
Mt. Joy 2026: Celebrating 10 Years Of Mt. Joy
Mt. Joy marks ten years with an October concert at the Huntington Bank Pavilion on Northerly Island.
Limited Run
#3Sat, Oct 3, 2026 · 8:00pm · Limited Run
Huntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West LoopMt. Joy 2026: Celebrating 10 Years Of Mt. Joy
Mt. Joy marks ten years with an October concert at the Huntington Bank Pavilion on Northerly Island.
Add to calendar#4
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopOnFirstWhoIs · CC BY-SA 3.0 · Wikimedia CommonsFri, Oct 2, 2026 · 8:00pmFrom $39
Freedom Riders with special guests Kurt Elling & Lizz Wright
Kurt Elling and Lizz Wright join this show at Orchestra Hall, tickets from $39.
One Day Only
#4Fri, Oct 2, 2026 · 8:00pm · One Day Only
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopOnFirstWhoIs · CC BY-SA 3.0 · Wikimedia CommonsFreedom Riders with special guests Kurt Elling & Lizz Wright
Kurt Elling and Lizz Wright join this show at Orchestra Hall, tickets from $39.
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#5
Sunday, October 4, 2026, 8:00 PM
Ludovico Einaudi
Ludovico Einaudi brings a solo-piano evening to Symphony Center on the first Sunday in October.
Limited Run
#5Sunday, October 4, 2026, 8:00 PM · Limited Run
Ludovico Einaudi
Ludovico Einaudi brings a solo-piano evening to Symphony Center on the first Sunday in October.
Add to calendar#6
Lyric Opera House, Loop, Downtown, the Loop & West LoopSunday, October 4, 2026, noonFree
2026 Final Auditions
Hear more than 20 emerging opera artists audition live and vote for the audience favorite.
FreeLimited Run
#6Sunday, October 4, 2026, noon · Limited Run
Lyric Opera House, Loop, Downtown, the Loop & West Loop2026 Final Auditions
Hear more than 20 emerging opera artists audition live and vote for the audience favorite.
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Bottom Lounge, West Loop, Downtown, the Loop & West LoopSunday, October 4, 2026, 7:00 PM (doors 6:00 PM)Ticketed via the venue
AJJ with Greet Death
AJJ with Greet Death has enough weekend energy to earn a spot on the board.
Limited Run
#7Sunday, October 4, 2026, 7:00 PM (doors 6:00 PM) · Limited Run
Bottom Lounge, West Loop, Downtown, the Loop & West LoopAJJ with Greet Death
AJJ with Greet Death has enough weekend energy to earn a spot on the board.
Add to calendar#8
Sat, Oct 3, 2026 · 7:30pm
Olivia O'Brien
Olivia O'Brien has enough weekend energy to earn a spot on the board.
Limited Run
#8Sat, Oct 3, 2026 · 7:30pm · Limited Run
#9
House of Blues Chicago, River North, Downtown, the Loop & West Loop#9Fri, Oct 2, 2026 · 7:00pm · Limited Run
House of Blues Chicago, River North, Downtown, the Loop & West Loop#10
Fri, Oct 2, 2026 · 7:00pm
Revocation, Defeated Sanity, Fuming Mouth, Weeping
Revocation, Defeated Sanity, Fuming Mouth, Weeping has enough weekend energy to earn a spot on the board.
Limited Run
#10Fri, Oct 2, 2026 · 7:00pm · Limited Run
Revocation, Defeated Sanity, Fuming Mouth, Weeping
Revocation, Defeated Sanity, Fuming Mouth, Weeping has enough weekend energy to earn a spot on the board.
Add to calendar#11
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West LoopSat, Oct 3, 2026 · 7:00pm
Heads In Motion (A Talking Heads Tribute) W/ Fluffy
Heads In Motion (A Talking Heads Tribute) W/ Fluffy has enough weekend energy to earn a spot on the board.
Limited Run
#11Sat, Oct 3, 2026 · 7:00pm · Limited Run
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West LoopHeads In Motion (A Talking Heads Tribute) W/ Fluffy
Heads In Motion (A Talking Heads Tribute) W/ Fluffy has enough weekend energy to earn a spot on the board.
Add to calendar#12
![Sinclair Noire, [Melter], Crash Davidian, Voltaic Planes, DJ Veganinbl](https://stumblday.com/api/image-assets/images/generated/chicago/ccd9df50e66e78a9ae923726c508d729cf86061c.png?w=480)
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West LoopSun, Oct 4, 2026 · 8:00pm
Sinclair Noire, [Melter], Crash Davidian, Voltaic Planes, DJ Veganinbl
Sinclair Noire, [Melter], Crash Davidian, Voltaic Planes, DJ Veganinbl has enough weekend energy to earn a spot on the board.
Limited Run
#12Sun, Oct 4, 2026 · 8:00pm · Limited Run
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West LoopSinclair Noire, [Melter], Crash Davidian, Voltaic Planes, DJ Veganinbl
Sinclair Noire, [Melter], Crash Davidian, Voltaic Planes, DJ Veganinbl has enough weekend energy to earn a spot on the board.
Add to calendar#13
Reggies Music Joint, South Loop, Downtown, the Loop & West LoopFriday, October 2, 2026; doors 8 p.m., show 9 p.m.
Daikaiju, 95 Bulls, PÜSSY
Daikaiju's psycho-surf meets 95 Bulls and PÜSSY for a late Reggies triple bill.
Limited Run
#13Friday, October 2, 2026; doors 8 p.m., show 9 p.m. · Limited Run
Reggies Music Joint, South Loop, Downtown, the Loop & West LoopDaikaiju, 95 Bulls, PÜSSY
Daikaiju's psycho-surf meets 95 Bulls and PÜSSY for a late Reggies triple bill.
Add to calendar#14
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopSat, Oct 3, 2026 · 8:30pm
Mourning Star, Rachel Is Kozi, Atta Guns
Mourning Star, Rachel Is Kozi, Atta Guns has enough weekend energy to earn a spot on the board.
Limited Run
#14Sat, Oct 3, 2026 · 8:30pm · Limited Run
Reggies Bananna's Shack, 2105 South State Street, Downtown, the Loop & West LoopMourning Star, Rachel Is Kozi, Atta Guns
Mourning Star, Rachel Is Kozi, Atta Guns has enough weekend energy to earn a spot on the board.
Add to calendar#15
Reggies Rock Club, 2109 South State Street, Downtown, the Loop & West LoopSat, Oct 3, 2026 · 6:00pm
Underground Madness
Underground Madness has enough weekend energy to earn a spot on the board.
Limited Run
#15Sat, Oct 3, 2026 · 6:00pm · Limited Run
Reggies Rock Club, 2109 South State Street, Downtown, the Loop & West LoopUnderground Madness
Underground Madness has enough weekend energy to earn a spot on the board.
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