Chicago-Area Live Music Recommendations for Oct. 8-14

Josh Terry | October 8, 2025, 5:00 am

TOPS (Credit: Aabid Youssef)

Each Wednesday, WTTW News producer Josh Terry presents must-see live music shows from indie rock to jazz, country, hip-hop and more.

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Wednesday, Oct. 8
Daarling, Stalled, Mourning Star at Empty Bottle. Tickets.
Pop into Ukrainian Village’s best bar and venue for a night of stellar indie rock.

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Thursday, Oct. 9
Goon, Beaming at Schubas. Tickets.
Two LA bands that write infectious songs with innovative rock arrangements.

Grandaddy, Greg Freeman at Thalia Hall. Sold out.
The Vermont-based opener has an album of the year contender in the searing rock LP “Burnover.”

Stereolab, Dorothea Paas at Metro. Sold out.
The iconic, genre-fusing art-pop band makes a triumphant two-show return to Chicago.

Hiss Golden Messenger, Rett Madison at Old Town School of Folk Music. Tickets.
This North Carolina folk singer is a can’t-miss show.

Charley Crockett at Salt Shed. Tickets.
A well-dressed country bard who is shaking up the genre.

Born Ruffians, Queen of Jeans at Subterranean. Tickets.
Toronto indie rock mainstays are more than 20 years into a fun career.

Friday, Oct. 10:
Laufey, Suki Waterhouse at United Center. Tickets.
An Icelandic-Chinese artist who proves that young people like timeless jazz singing.

Sink, Conor Lynch, Dogcatcher at Cole’s. Tickets.
A Columbus songwriter who plays in the great band Villagerrr caps off this stacked bar bill.

Chance the Rapper, Do or Die, Taylor Bennett at Northerly Island. Tickets.
The hometown hero is back with a new album called “Star Line.”

Addison Rae at Aragon Ballroom. Tickets.
Ask a Zoomer in your life about this artist.

Stereolab, Bitchin Bajas, Natural Information Society at Metro. Sold out.
The iconic, genre-fusing art-pop band makes a triumphant two-show return to Chicago.

Saturday, Oct. 11:
Nico Segal (& The Social Experiment), The O’Mys, more at Metro. Tickets.
The Chicago musicians celebrate 10 years of the mixtape “Surf.”

Richy Mitch and the Coal Miners, Field Medic at Salt Shed. Tickets.
Get there early for the charming folk-pop of opener Kevin Patrick Sullivan.

Model/Actriz, Kassie Krut at Lincoln Hall. Tickets.
Innovative, danceable and pummeling synth-rock across the lineup here.

Aly & AJ, Amanda Shires at Salt Shed. Tickets.
A bill of excellent songwriting and girls rocking.

Dan English, Alive Girl, Thinking About It at Empty Bottle. Tickets.
This New York City musician has collaborated with Porches and Melody English but also makes excellent solo music.

Sunday, Oct. 12:
Qunnie, Operelly at Lincoln Hall. Tickets.
This New Jersey rocker is touring her album “paper doll.”

Tuesday, Oct. 14:
TOPS, Starcleaner Reunion at Thalia Hall. Tickets.
Timeless pop from a locked-in Montreal band.

After at Lincoln Hall. Sold out.
Like the 2000s? This young indie pop band puts the contemporary in “adult contemporary.”