The Salt Shed/Photo: John Bender

1
Warm Love Cool Dreams
(The Salt Shed)
The festival named after a Nelson Algren line returns with a mix of hometown favorites like Tortoise and Whitney plus headliners like The Jesus and Mary Chain and Courtney Barnett.
May 23-24

2
Mike Reed’s Chicago Inspirations
(Symphony Center)
Mike Reed’s universe comes downtown, curating a program called “The Magic Box” honoring AACM bassist Fred Hopkins, plus a collection of jazz works composed in Chicago between 1980 and 2010.
May 1

3
Chicago Jazz String Summit 2026
(Constellation, Hungry Brain)
A week later, Reed’s Bricktown venues host the annual springtime summit dedicated to string players in jazz, this year honoring 1970s Amsterdam free improv figure Tristan Honsinger.
May 8-10

4
Gia Margaret
(Thalia Hall)
The Chicago-based singer-songwriter plays Thalia Hall in support of “Singing,” a brand new album from Jagjaguwar. Read our feature on Margaret in the May issue for more on the occasion.
May 12

5
Griffin Brown, Zander Raymond, Paige Alice Naylor
(The Hideout)
Poet-musician Griffin Brown is joined by Chicago-based artists Paige Alice Naylor, an experimental vocalist, and Zander Raymond, a visual artist and synthesist.
May 28