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Nashville recording artist Dylan Raymond is bringing his 2026 tour to Stolen Saddle in Chicago, IL on Saturday, January 10th at 10:00 PM! Raised in Indiana on a steady diet of ’90s country, Dylan picked up a guitar at just eight years old and never put it down. Today, he’s known for his signature voice, high-energy live shows, and a sound that blends modern country punch with classic country soul.
From honky-tonks to sold-out amphitheaters, Dylan’s rise has been fueled by the road. His breakout single “I Can Be That” climbed the country charts and has racked up millions of streams, followed by fan-favorite releases like “Til the Cows Come Home,” earning spots on major Spotify playlists including New Music Friday.
Dylan has shared the stage with some of the biggest names in country music, including Jake Owen, Gabby Barrett, Russell Dickerson, Trace Adkins, Diamond Rio, Aaron Tippin, Collin Raye, Jordan Davis, Chris Janson, and more — and has performed on iconic stages like CMA Fest and Whiskey Jam in Nashville.
After headlining 75+ acoustic shows in 2023, 120+ shows nationwide in 2024, and 130+ dates in 2025—including tours with Gabby Barrett and Russell Dickerson—Dylan Raymond hits 2026 with more momentum than ever.
Whether you’ve been following him for years or you’re hearing his name for the first time, this is your chance to catch one of country music’s fastest-rising artists up close.
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Event Venue & Nearby Stays
Stolen Saddle, 3505 N Clark St, Chicago, IL 60657-1611, United States
Concerts, fests, parties, meetups - all the happenings, one place.
