Up! Live in Chicago is the third live video album by Canadian singer Shania Twain. Directed and produced by Beth McCarthy-Miller, the concert was held and filmed on July 27, 2003 at Hutchinson Field in the south-side of Grant Park in Chicago, Illinois; over 50,000 people attended. The concert itself differed from that of the Up! Tour (2003–04), featuring a different stage, setlist and production. Behind-the-scenes footage of the singer visiting local landmarks and events was filmed the same week. The concert film premiered on the National Broadcasting Company (NBC) on August 19, 2003. The special was watched by over 8.87 million viewers, becoming the second-most-viewed concert film on television, behind Celine Dion's A New Day ... Live in Las Vegas (2003).

Due to its high television ratings, Up! Live in Chicago was released as a video album on November 18, 2003 by Mercury Records Nashville. Released both in standard DVD packaging and in a jewel case, it featured additional performances not included on the television presentation. The album was also received positively by music critics, who complimented Shania's interaction with the audience; however, some questioned her live singing. The video peaked at number two on Billboard's Top Music Video sales chart, and was certified platinum by the RIAA for shipments of over 100,000 copies in the United States. It was also certified platinum in Australia and gold in Austria and Brazil. Excerpts from Up! Live in Chicago were used as the music videos for "She's Not Just a Pretty Face" (2003) and "It Only Hurts When I'm Breathing" (2004).