City Winery

A singer, composer and actor, Lyle Lovett has broadened the definition of American music in a career that spans 14 albums. Coupled with his gift for storytelling, the Texas-based musician fuses elements of country, swing, jazz, folk, gospel and blues in a convention-defying manner that breaks down barriers. Lovett's live performances show not only the breadth of this Texas legend's deep talents, but also the diversity of his influences, making him one of the most compelling and captivating musicians in popular music. Since his self-titled debut in 1986, Lyle Lovett has evolved into one of music's most vibrant and iconic performers. Among his many accolades, besides the four Grammy Awards, he was given the Americana Music Association's inaugural Trailblazer Award, and was named Texas State Musician. His works, rich and eclectic, are some of the most beloved of any artist working today.

from $162

A singer, composer and actor, Lyle Lovett has broadened the definition of American music in a career that spans 14 albums. Coupled with his gift for storytelling, the Texas-based musician fuses elements of country, swing, jazz, folk, gospel and blues in a convention-defying manner that breaks down barriers. Lovett's live performances show not only the breadth of this Texas legend's deep talents, but also the diversity of his influences, making him one of the most compelling and captivating musicians in popular music. Since his self-titled debut in 1986, Lyle Lovett has evolved into one of music's most vibrant and iconic performers. Among his many accolades, besides the four Grammy Awards, he was given the Americana Music Association's inaugural Trailblazer Award, and was named Texas State Musician. His works, rich and eclectic, are some of the most beloved of any artist working today.

from $162

A singer, composer and actor, Lyle Lovett has broadened the definition of American music in a career that spans 14 albums. Coupled with his gift for storytelling, the Texas-based musician fuses elements of country, swing, jazz, folk, gospel and blues in a convention-defying manner that breaks down barriers. Lovett's live performances show not only the breadth of this Texas legend's deep talents, but also the diversity of his influences, making him one of the most compelling and captivating musicians in popular music. Since his self-titled debut in 1986, Lyle Lovett has evolved into one of music's most vibrant and iconic performers. Among his many accolades, besides the four Grammy Awards, he was given the Americana Music Association's inaugural Trailblazer Award, and was named Texas State Musician. His works, rich and eclectic, are some of the most beloved of any artist working today.

from $162

Michael Lington, “On The Scene” Over 25 years into his extraordinarily impactful, hit-studded career, Michael Lington made Billboard chart history, building on his legacy of smash singles with “South Bay,” from his 2023 EP “Looking Ahead”. It is the longest running #1 on the Billboard Smooth Jazz Airplay chart and it took only four weeks to reach the pole position, where it stayed for a record setting seven weeks! Fully embodying the hip, spontaneous action and energy promised in it’s title, Lington’s latest track “On the Scene” – the first lead single from his upcoming album – keeps the party going with a fresh and fiery, funked out and horn drenched jam that perfectly captures the spirit of the early days of contemporary Jazz, but with a modern sound. Co-produced and composed by Lington and veteran saxman, arranger and producer David Mann, the song features the same powerhouse crew that brought the magic to his recent Billboard Top 5, “Moon Goddess” – guitarist Paul Jackson, Jr., bassist Alex Al and drummer Michael White.

from $48

Kate Voegele Kate Voegele is an LA based singer/songwriter, recording artist, and content creator. She is also an actress, starring on the hit CW show 'One Tree Hill,' a painter, and business owner of the blog and lifestyle company We The Dreamers. Along with playing thousands of shows touring internationally for the last decade, Voegele has released 4 studio albums to date, selling over 500,000 copies in total and racking up millions of streams. In addition to her most recent release, “The Best Part (French Version),” a single in collaboration indie band Bien, Kate has recently released several singles with her band, Your Future Ghost, in anticipation of a debut album drop this summer. Tyler Hilton From portraying Elvis Presley in Walk the Line and garnering a cult following as musician Chris Keller on the CW hit TV show One Tree Hill, to writing and touring with the likes of Taylor Swift, Lady Antebellum and Joe Cocker, Tyler Hilton has enjoyed an award-winning career spanning music, film and television. Born and raised in California, Tyler grew up in a family of talented musicians who had played for acts like Fleetwood Mac, George Harrison and Donovan. Performing with his family from an early age, Hilton became serious about songwriting at 14. At 15, he called into L.A.’s KLOS radio station to win concert tickets and ended up wowing the hosts with an on-air performance. The station made him a regular guest and helped launch his debut record, which caught the ear of Warner Bros. Records, who signed him to record his second album The Tracks of Tyler Hilton, earning him two Top 40 singles.

from $36

Kevin Ross is a Grammy-nominated singer, songwriter, producer, and performer from Washington, D.C., celebrated for his smooth vocals, heartfelt storytelling, and genre-blending vision. Since his breakthrough with “Long Song Away,” Ross has built an impressive catalog, collaborated with icons like Babyface, Toni Braxton, and Trey Songz, and headlined sold-out shows nationwide. In 2019, he founded his own label, Art Society Music Group, championing independence and creative freedom. His 2025 single “Love In The Middle” became his first #1 as an indie artist, holding the top spot on Billboard’s Adult R&B Airplay Chart for three consecutive weeks. Known for powerful performances, including Noochie’s Live From The Front Porch and Yams Sessions, Ross continues to push R&B forward with his album, LOVE UPTEMPO: MAX.

from $66

City Winery Chicago Presents Nathan Chester & The Old Soul’s Motown Revival Brunch on Sunday, June 14th at 12:00 PM! Nathan Chester & The Old Soul’s Motown Revival — a high-energy, artist-led show that reimagines soul music through a punchy, horn-driven Motown lens. Think Postmodern Jukebox’s inventive spirit, but with a Motown vibe: vintage grooves, modern production, and a commanding lead vocal that fills theaters and dance floors alike. Chester is committed to creating soul music that makes you feel and dance. With his new tour Nathan Chester @ the Old Soul Motown Revival, Nathan continues his exploration of the Soul Classics from Motown, Stax, and Muscle Shoals era’s as well as showcasing his new soul music. Nathan Chester, Chicago native, is not just a singer but a multifaceted artist and entrepreneur. Presently residing in Nashville, Nathan’s journey into the spotlight began on NBC’s The Voice Season 25, where his soulful rendition of Al Green’s “Take Me to the River” captured the attention of John Legend and Dan + Shay, ultimately leading him to join Team Legend.  What a soulful, powerful voice,” Legend has said of Chester. “I love that he’s so committed to this throwback, soulful style. You can just tell he’s not afraid of the moment. I think Nathan’s gonna go far.” Throughout the competition, Nathan’s performances were marked by their cinematic quality and powerful delivery, earning him accolades and a strong fan following. He showcased his vocal prowess with covers ranging from Soul classics “Try a Little Tenderness”, “When a Man Love’s a Woman”, and “It’s Your Thing” to contemporary hits like Adele’s “Rolling in the Deep.” His journey culminated in a top-four finish, cementing his place as a standout artist in the season 25, 2024. Beyond his musical achievements, Nathan is rooted in his hometown of Chicago, where he attended Oak Park and River Forest High School before pursuing a musical theater degree at Waldorf University. His dedication to his craft and entrepreneurial spirit are evident in his aspirations as a singer-songwriter and actor. Alongside his girlfriend, Emily Viancourt, he co-founded Em & N Productions, where they curate performances for various venues including cruises and private events. Nathan and Emily’s ambition extends beyond performance, aiming to expand their production company and support fellow artists’ post-show. Offstage, Nathan enjoys connecting with his community returning to Chicago for the first time since The Voice with performances including Wrigley Field and engaging with local schools. His story is one of perseverance and passion, driven by a love for music that continues to inspire audiences worldwide. Follow Nathan’s journey and original music on Instagram @nathan_chesterr, where he shares updates on upcoming performances and projects with Em & N Productions.

from $30