Live in Chicago marks Ween's second widely distributed live album (their fifth overall when counting the limited-edition releases put out on their home record label Chocodog Records), the first Ween DVD, and the second album overall they've released on Sanctuary Records. It was released on May 4, 2004 and performed at The Vic Theatre in Chicago, Illinois, USA.
Packaged alternately as a CD with bonus DVD or a DVD with bonus CD, Live in Chicago documents two nights of a show the group did in Chicago in support of their album Quebec. The DVD features a wide variety of Ween songs, covering nearly every Ween album except 12 Golden Country Greats and even features a cover of the Led Zeppelin classic "All of My Love". Also, the DVD contains alternate camera angles for three of the performances, and a bonus music video for the song "Transdermal Celebration".
The CD, in comparison, contains fewer songs and a different track list.