Arts & Entertainment
Chicago-Area Live Music Recommendations for May 20-26
Courtney Barnett (Lindsey Byrnes)
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, May 20:
Twin Peaks, Finn Wolfhard at Thalia Hall. Sold out.
The beloved, reunited Chicago rock band gets an assist from a talented, young actor, director and musician as an opener.
Anjimile, Oyeme at Hideout. Tickets.
This North Carolina artist’s intimate and revelatory songs can quiet the rowdiest audience.
Quiet Light, Lipsticism at Schubas. Tickets.
Immersive, eerie and mesmerizing electropop in Lakeview.
Thursday, May 21:
Twin Peaks, Post Animal at Thalia Hall. Sold out.
Eight shows in eight days for the Chicagoans will close with a bang, featuring another fantastic local opening band that was inspired by the headliners.
Trash Kickers, Pleaser, Joe Glass at Schubas. Tickets.
A raucous collection of local talent gathers in Lakeview to celebrate the release of the headliners’ new LP, “Way Out.”
Zander Raymond, Tyler Wagner and Zander Raymond Duo at Judson and Moore. Tickets.
Improvisational, patient music at a cozy Avondale distillery.
Just Mustard, Miss Grit at the Empty Bottle. Sold out.
By the end of this hotly anticipated sold-out Chicago show, the Irish headliners might have to change their name to “Dragged Through the Garden.”
Friday, May 22:
Hum, Nothing, Chapterhouse, she’s green, Total Wife at Aragon Ballroom. Tickets.
Slide Away Fest is a two-day festival in Uptown featuring some of the most exciting names in indie rock, shoegaze and more.
Portrayal of Guilt, Street Sects, Halloween, Smut at Empty Bottle. Tickets.
Loud, aggressive and explosive music in a Ukrainian Village venue that’s best suited for that.
The Orchard, Dogs With Hats, Poolish at Schubas. Tickets.
Rock music at its most folky and countryfied performed by locals at a Lakeview venue.
Saturday, May 23:
Lone Rock Bride, The Part Timers at Judson and Moore. Tickets.
Want some twang? Head to Avondale for a solid bill of Americana-tinged rock music.
The Jesus and Mary Chain, Pixel Grip, Tortoise, Smerz, YHWH Nailgun, Kumo 99, Mark William Lewis at Salt Shed. Tickets.
Warm Love Cool Dreams is a two-day music festival named after a line in Nelson Algren’s “The Man With the Golden Arm” that showcases innovative acts from around the world in electronic, indie rock, pop and more.
Hum, Nothing, Chapterhouse, loveliescrushing, Cloakroom, Sunshy at Aragon Ballroom. Tickets.
Slide Away Fest is a two-day festival in Uptown featuring some of the most exciting names in indie rock, shoegaze and more.
Sunday, May 24:
IML Queen! at Metro and smart bar. Sold out.
An all-building event featuring DJs the Carry Nation, Derrick Carter, Josh Caffé, Michael Serafini and more hits Wrigleyville for a Memorial Day weekend dance party.
Courtney Barnett, Whitney, Toro y Moi, Nourished By Time, Moin, Being Dead, Tobacco City, Lauren Auder at Salt Shed. Tickets.
Warm Love Cool Dreams is a two-day music festival named after a line in Nelson Algren’s “The Man With the Golden Arm” that showcases innovative acts from around the world in electronic, indie rock, pop and more.
Tuesday, May 26:
Modern Cults, Mildred, Josh Leahy and The Phonebook at Empty Bottle. Tickets.
Mildred, the wildly collaborative Bay Area folk rock band, might have this newsletter producer’s favorite LP of 2026.
WTTW News arts coverage is supported by the JCS Arts, Health & Education Fund of the DuPage Foundation.
