Andrew Bird, Kelsey Waldon and 10 other great May concerts in Chicago

Our monthly concert list curates great picks mostly from midsize and neighborhood venues.

Andrew Bird
The Andrew Bird Trio is one of the many concerts that will grace Chicago stages this May. John Davisson/Invision/Associated Press
Andrew Bird
The Andrew Bird Trio is one of the many concerts that will grace Chicago stages this May. John Davisson/Invision/Associated Press

Andrew Bird, Kelsey Waldon and 10 other great May concerts in Chicago

Our monthly concert list curates great picks mostly from midsize and neighborhood venues.

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For Chicago audiences, May’s slate of musical choices brings some local perennials, cult favorites from across the pond and emerging voices in country and blues. Here’s what to look forward to this month.

Teenage Fanclub with Sweet Baboo

8 p.m. May 5 at Thalia Hall

For 35 years, Scotland’s Teenage Fanclub has consistently delivered catchy jangle-pop drowning in fuzz guitar and warm vocal harmonies. The latest, Nothing Lasts Forever, is no reinvention — but confirmation that the formula still works. Like bands Crowded House and Squeeze, Teenage Fanclub is rooted in tracks laid by the Beatles and Big Star. But, over time, the themes in the music have evolved into the big life questions and dilemmas that come from your middle years. 1807 S. Allport St., tickets from $28.

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Kelsey Waldon

8 p.m. May 8 at Carol’s Pub

One of the most exciting new voices in country music today, Kelsey Waldon was signed to John Prine’s Oh Boy Records not long before the songwriter’s death in 2020; she’s one of only three artists to be signed to the label in decades. Originally from rural Kentucky, Waldon’s first four albums were acclaimed for their confessional lyrics drawn from her childhood, a heavy vocal twang and an omnipresent rocking beat. Her latest album, There’s Always a Song, is a collection of favorite country and bluegrass standards that pair her with likeminded souls — think Margo Price, Amanda Shires and S.G. Goodman. Catch her at this cozy corner honkytonk before an inevitable future playing the bigger rooms. 4659 N. Clark St., tickets from $18.

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Jackie Venson

8:30 p.m. May 16 at FitzGerald’s

There are not many emerging voices so singular on the neo-blues scene than guitarist Jackie Venson whose music is rooted in the genre, but like Gary Clark Jr. and others, incorporates soul music, electronics, and honkytonk in her playing. She has released four albums, the most recent a remix record of her song catalog to date. Venson’s approach to dynamic guitar style and songwriting doesn’t follow the usual tropes; she has already proven to be an artist who easily crosses over into multiple genres without sounding like she’s just visiting. 6615 W. Roosevelt Rd., tickets from $25.

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Ride with Knifeplay

7:30 p.m. May 16 at Metro

British shoegaze pioneers Ride came to prominence in the early 1990s by forging a sound that combined psychedelia and the gnarly guitar play of peers like My Bloody Valentine and Sonic Youth. The group reunited nearly a decade ago and, like Slowdive, Pixies and The Jesus and Mary Chain, got reenergized to make new music that stands up to, and even surpasses, the band’s first phase. Released in March, Interplay has many of the elements of their first act — psychedelic flourishes and crashing guitars — but this second act also introduces new explorations into synth-pop, sampling and trip-hop beats. 3730 N. Clark St., tickets from $40.

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Dianne Reeves and Chucho Valdés with Joe Lavano

8 p.m. May 17 at Symphony Center

An all-star concert featuring three jazz legends: jazz vocalist Dianne Reeves, Afro-Cuban jazz pianist and composer Chucho Valdés and saxophonist Joe Lavano. Reeves and Valdes will perform a series of duets together, accompanied by Lavano. 220 S. Michigan Ave., tickets from $45.

Naomi Ashley
Naomi Ashley will open for pat mAcdonald in Chicago this May. Taylor Glascock for WBEZ

pat mAcdonald with Naomi Ashley and Jon Williams

7:30 p.m. May 18 at the Friendly Community Room

pat mAcdonald was one-half of Timbuk3, the groundbreaking late 1980s duo that made a splash in the MTV era by combining electronic beats with folk guitars and a sardonic sense of humor — a precursor to Beck, eels and other groups a decade later. After a lengthy solo career, with songs covered by everyone from Aerosmith to Cher, MacDonald moved to Door County, Wis., where he now runs the Holiday Music Motel, a lodge, venue, and recording studio. Still, he’s back playing shows in quiet listening rooms around the Midwest. Opening this show is Chicago singer-songwriter Naomi Ashley and her music collaborator Jon Williams.

6729 Roosevelt Rd., Berwyn, tickets from $20.

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Bethany Thomas

8:30 May 22-24 at Constellation

Bethany Thomas is well known to both music and theater audiences in Chicago for her own original music and roles in acclaimed dramas and musicals at the Goodman Theatre, Writers Theatre and Chicago Shakespeare. This three-night stand transports Thomas and her six-piece band into the 1970s glam rock scene where she will perform the songs of Transformer, Lou Reed’s seminal 1972 album produced by both David Bowie and Mick Ronson. Considered one of the greatest albums of the decade, and certainly of Reed’s career, it also produced his breakthrough to the mainstream thanks to singles “Walk on the Wild Side,” “Vicious” and “Satellite of Love.” 3111 N. Western Ave., tickets from $35.

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Don Was

6 p.m. and 9 p.m. May 22 at Space

Don Was is a bassist, veteran bandleader (Was Not Was), Grammy-winning record producer (Bob Dylan, the Rolling Stones, Bonnie Raitt) and the president of a historic jazz label (Blue Note Records). In recent years, he’s been on the tour circuit with Bob Weir of the Grateful Dead. He’s also originally from Detroit, a city he honors through his latest project, Don Was and the Pan-Detroit Ensemble, an eight-piece collective of jazz musicians from his hometown including saxophonist Dave McMurray, vocalist Steffanie Christi’an and Eminem keyboardist Luis Resto. Together they’ll perform a mix of originals, covers and selections from past Was albums. 1245 Chicago Ave., Evanston, tickets from $35

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Buck Meek
Buck Meek, the lead guitarist of Big Thief, will perform solo at Lincoln Hall this May. Anthony Vazquez/Chicago Sun-Times

Buck Meek with Jolie Holland

8 p.m. May 24 at Lincoln Hall

This is a solo show featuring Buck Meek, best known as the lead guitarist of Big Thief, the lo-fi Americana band from Brooklyn that released five albums over the last decade. His own fragile-sounding work doesn’t have the noisy or fragmented spirit of that band. Instead, the charms of his recent album Haunted Mountain are in the more straightforward arrangements, cheery pop hooks and playful psychedelic backdrop. Opening is Texas singer-songwriter Jolie Holland, whose latest album is also titled Haunted Mountain and features five songs co-written with Meek, including the title song that appears on both records. That’s synergy. 2424 N Lincoln Ave., tickets from $25.

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Melody Angel

9:30 p.m. and 11:30 p.m. May 24 at Rosa’s Lounge

Guitarist and singer Melody Angel is among the new generation of blues musicians in Chicago who is taking the music to a new level, combining funk, soul, and hip-hop. Her most recent album is She Black from 2021. 3420 W. Armitage Ave., tickets from $25.

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Luke Winslow-King

6:30 p.m. May 24 at Robert’s Westside

Expect a full band concert by this singer-songwriter whose music evokes early jazz and vintage country blues. The one-time New Orleans resident made his name through a long run of albums on Chicago’s Bloodshot label, and on Bloodshot, he established himself as a compelling lyricist, master slide guitarist and fully engaged interpreter of early-century music. If These Walls Could Talk, his most recent record, was recorded in Memphis and features more pop-driven songs and appearances by locals including the Sensational Barnes Brothers, a gospel duo. 7321 Madison St., Forest Park, tickets from $20.

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The Andrew Bird Trio

6:30 and 9 p.m. May 29 at the Green Mill and 8 p.m. May 31 at the Old Town School of Folk Music

North Shore native Andrew Bird returns to Chicago to play two shows on the North Side — including one at the Uptown jazz club he frequented when heading the Bowl of Fire, his early group in the 1990s. After a long string of albums, the fiddler-songwriter-whistler is returning to his roots with Sunday Morning Put-On, a new album released this month. He describes it as a collection of jazz standards inspired by his love of the music that began when he lived in Edgewater and listened to early jazz and blues shows on WBEZ and WDCB. Green Mill, 4802 N. Broadway Ave., and Old Town School, 4544 N. Lincoln Ave., tickets from $70.

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Mark Guarino is a journalist based in Chicago and the author of Country & Midwestern: Chicago in the History of Country Music and the Folk Revival.