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Simon in Chicago

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About Simon

Simon is one of those artists who somehow manages to be both impossibly prolific and genuinely experimental. His catalog spans folk-rock foundations to world music collaborations to synth-driven pop, often within the same album. He's got this thing where he'll disappear into a project—a South African township collaboration, a Subway Stories documentary score—and come back with something that shouldn't work but does. What keeps people coming back is that underneath all the genre-hopping and studio tinkering, there's a genuinely precise way he writes about mundane moments and makes them feel like they mean something. The man's been making albums for fifty years and still seems more interested in solving compositional puzzles than in being a rock star, which is probably why people still take him seriously.

His shows are attentive, almost scholarly. The crowd leans in rather than loses it. He'll adjust arrangements on the fly, try new versions of old songs. You get the sense he's still working through ideas onstage. People don't scream; they listen.

Known for You Can Leave Your Hat On, The Obvious Child, Graceland, Call Me Al, The Boy in the Bubble

Simon + Chicago

Simon has built a quiet presence in Chicago's music scene over the years. The artist stopped by The Hideout in September 2025, continuing a pattern of intimate performances in the city. These smaller venues seem to suit Simon's restrained approach to songwriting and performance, letting the songs breathe in rooms where people actually listen.

Simon in Chicago News

Live Music in Chicago

Chicago's music scene has always been built on artists doing their own thing. Whether it's the legacy of experimental electronic producers, indie rock that refuses to play it safe, or singer-songwriters carving out their own path, the city rewards specificity over broad appeal. That ethos makes Chicago a natural fit for artists working in folk, indie, and alternative spaces who aren't chasing trends.

Chicago road trip to see Simon?

Stay in Lincoln Park or Wicker Park depending on your vibe—both neighborhoods have real character and plenty of late-night options. Book dinner at Alinea if you're feeling ambitious, or hit RPM Italian for something excellent and less impossible to get into. Spend an afternoon at the Art Institute, then walk along the Lakefront. The city's got enough to fill a weekend without feeling like you're checking boxes. Catch the show, eat well, and remember why you liked this band in the first place.

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