Rilo Kiley performs at The Chicago Theatre in Chicago on May 29, 2026.
Rilo Kiley performs at The Chicago Theatre in Chicago on May 29, 2026.

Who doesn’t love nostalgia? Looking back on a place and time creates a beautiful medley of emotions. It’s no wonder that reunion tours are a popular way to reconnect with our favorite bands and our past selves.

Some bands may reunite as a way to both satisfy fans and make some easy money, others use these tours as a way to build upon their legacy as older, wiser, more complex artists while still staying true to their roots. With their Sometimes When You’re On You’re Really Fucking On Tour – which built upon the success of the 2025 run with a handful of dates in 2026 – Rilo Kiley has turned the idea of the reunion tour on it’s head.

At the band’s May 29 show at The Chicago Theatre in Chicago, each song sounded as flawless as fans remember from the studio albums. And yet – through a combination of intricate jams, refined musicianship, and emotional depth – Jenny Lewis (vocals, keys, guitar, bass), Blake Sennett (guitar, vocals, keys), Pierre de Reeder (bass, guitar, and even the triangle), Jason Boesel (drums), and touring multi-instrumentalist Harrison Whitford delivered a performance that was somehow better than perfect.

Rilo Kiley performs at The Chicago Theatre in Chicago on May 29, 2026.
Rilo Kiley performs at The Chicago Theatre in Chicago on May 29, 2026.

After an earnest opening set by singer-songwriter Jean-Luc Eldenwood, fans rose to their feet as Rilo Kiley’s show began with the title track off the group’s sophomore album, The Execution of All Things. “The Moneymaker,” “Spectacular Views,” and the Sennett-led “Dreamworld” appeared early in the set. The ladies in the crowd couldn’t get enough of “I Never” unleashing woos throughout as Lewis bared her soul and showed off her vocal range.

“Does He Love You?” was one of the many stand-outs of the night as the entire band came together, physically closing the distance between each other on the stage, as their vocals and instruments swelled with sound and emotion. Lewis serenaded fans in the front row while Whitford’s keys added to the instrumental Beatles vibes coming from Sennett’s weeping guitar. The rhythm section of de Reeder and Boesel emerged at the forefront of the songs patiently built outro leading the way to a climactic, and unforgettable, conclusion.

Rilo Kiley performs at The Chicago Theatre in Chicago on May 29, 2026.
Rilo Kiley performs at The Chicago Theatre in Chicago on May 29, 2026.

Later, Lewis and de Reeder appeared to be having as much fun as fans were while Sennett strummed the sweet, melancholy music of “Ripchord,” another song that was elevated by an enhanced, complex arrangement featuring the whole band. “The Good That Won’t Come Out” felt like opening a time capsule, sending everyone on a trip back to 2002 while somehow anchoring the moment in the present.

Before sharing a three-song encore, the set came to it’s conclusion with a pair of fan favorites – “A Better Son/Daughter” and “Portions for Foxes” – that had everyone singing every single word and loving every nuanced musical and lyrical phrase pouring off the stage. The latter tune provided yet another example of how much this band has grown musically, from indie darlings to powerhouse players, with an extended coda that set the stage for the best jam of the performance.

Rilo Kiley performs at The Chicago Theatre in Chicago on May 29, 2026.
Rilo Kiley performs at The Chicago Theatre in Chicago on May 29, 2026.

“Chicago, you guys really kick ass,” said Sennett as the set neared it’s end. “I think I speak for all of us when I say, ‘We love you very much.’”

Rilo Kiley is heading across the pond for a handful of dates in June. There has been no word as of yet if this will be the end of the reunion run, but we hope the band comes back for more. Even if it takes another 17 years between tours, with Rilo Kiley the wait is most definitely worth it.

(Photos by Laurie Fanelli)

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Laurie Fanelli is a Chicago-based writer and photographer who specializes in live entertainment coverage. She is at home at major music festivals like Coachella, Bonnaroo and, of course, Lollapalooza and...