Get ready to enjoy a memorable night with Cassadee Pope at City Winery - Chicago on January 24, 2026, where her captivating pop/rock melodies will light up the venue. Meanwhile, fans of Sarah McLachlan can mark their calendars for November 22, 2025, at the Auditorium Theatre - IL, an evening sure to resonate with heartfelt performances. For a unique twist, don't miss the Squirrel Nut Zippers on December 11, 2025, at Park West, where their eclectic sound promises to be a delightful experience. Later that spring, on April 11, 2026, Loudon Wainwright III & Chris Smither will take the stage at the Gary & Laura Maurer Concert Hall at Old Town School of Folk Music, blending storytelling with soul-stirring melodies. Also, keep an eye out for Sting, returning to the Auditorium Theatre - IL on November 24, 2025, ready to deliver an unforgettable night of classic hits. For more information on these events and to explore ticket options, visit ticketschicago.net, your go-to for Chicago concerts and experiences that resonate with fans.