Chicago-Area Live Music Recommendations for Oct. 21-27

Josh Terry | October 21, 2026, 5:00 am

Wishy (Rian Archer)

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. 21:
Moontype, Raul Cotaquispe, Audrey at Color Club. Tickets.
Moontype’s Margaret McCarthy headlines this Old Irving Park show with a solo set.

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The Tubs, Mopar Stars at Empty Bottle. Tickets.
The self-described “Celtic jangle boy band” brings their anthemic and rousing brand of indie rock to Ukrainian Village.

Dogwood Tales, The Part Timers at Gman Tavern. Tickets.
The Virginia country rockers enlist a promising local rock band to open.

DJ Shadow, Open Mike Eagle at The Vic Theatre. Tickets.
Josh Davis returns to the city this month for a second concert celebrating the 30th anniversary of his critical masterpiece LP “Endtroducing.....”

Thursday, Oct. 22:
Whitney, Greg Mendez at Metro. Tickets.
The Chicago folk rock band plays the Lakeview venue for the first time since 2017.

Sylvan Esso, Sen Morimoto at Salt Shed. Tickets.
Synth-rock heroes bring a multi-talented Chicagoan to open.

Ovven, Samuel Aaron, Glass Beagle at Beat Kitchen. Tickets.
Look up what some music critics call “indie twang,” and you’ll see this Roscoe Village show in the dictionary.

LeRoy Bach + Dan Bitney at Sleeping Village. Tickets.
Two veterans of Chicago’s rock and experimental music scenes team up for a duo set.

Friday, Oct. 23:
Gilla Band, Piss at Bottom Lounge. Tickets.
This Irish band makes music at the intersection of discordant and danceable.

Tedeschi Trucks Band at Chicago Theatre. Tickets.
Southern fried jam heroes plot a mini-residency at the legendary Loop venue.

Cosmic Country Showcase at Empty Bottle. Tickets.
The best variety show and country concert series returns, featuring Dougie Poole, Elizabeth Moen, and more.

Saturday, Oct. 24:
Tedeschi Trucks Band at Chicago Theatre. Tickets.
Southern fried jam heroes plot a mini-residency at the legendary Loop venue.

Greg Freeman, Hello Shark at Lincoln Hall. Tickets.
The acclaimed and now Chicago-based rocker plays his first “hometown show” as a recent resident.

Mobb Deep, Talib Kweli at Ramova Theatre. Tickets.
Two hip-hop titans join forces in Bridgeport.

Fruit Bats, Matthew Logan Vazquez at Salt Shed. Tickets.
The folk rock band that started in Chicago has found new and larger audiences recently thanks to timeless songs.

Sunday, Oct. 25:
Autobahn, Godstar Megamix at Lincoln Hall. Tickets.
Spend your Sunday with boundary-pushing acts at a cozy venue.

Monday, Oct. 26:
Tedeschi Trucks Band at Chicago Theatre. Tickets.
Southern fried jam heroes plot a mini-residency at the legendary Loop venue.

Tuesday, Oct. 27:
Worldpeace DMT at Schubas. Tickets.
Some music critics have called this London duo “laptop twee,” but they defy expectations on their latest LP “Stick Around for Tea.”

Wishy, Dead Sullivan, Sacred Heart Academy at Lincoln Hall. Tickets.
The Indiana indie rock band thrives on massive hooks and punchy energy.

Colin Miller at Hideout. Tickets.
You might know this musician as MJ Lenderman’s drummer, but he’s a fantastic solo songwriter and the heart of the burgeoning Asheville music community.

Wide Orbit, Disiac, Big Smudge at Empty Bottle. Tickets.
This Chicago band elevates bar rock with stellar songwriting.

This Is Lorelei, @ at Thalia Hall. Sold out.
The hottest ticket in indie rock this week.

WTTW News arts coverage is supported by the JCS Arts, Health & Education Fund of the DuPage Foundation.