In early 2007, Wilco was in the midst of promoting their album "Sky Blue Sky," which was released later that same year. This live recording of "Via Chicago" captures the band's performance at a special pop-up concert at the Chicago Athletic Association’s Stagg Court, underscoring their deep roots in the Chicago music scene. "Sky Blue Sky" marked a significant shift for Wilco, as it showcased a more straightforward, roots-oriented sound compared to their previous work, which often included experimental elements. The band was known for their evolution and willingness to explore different musical directions, and performing at intimate venues like this one highlighted their connection with fans during this transitional period. Additionally, the Songkick Live concert format offered a unique opportunity for audiences to experience live music in a more direct and personal setting.