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).
| Actor | Role |
|---|---|
 Shania TwainSelf | Self |
| BBrent BarcusSelf - Guitars | Self - Guitars |
| JJ.D. BlairSelf - Drums | Self - Drums |
| RRoddy ChiongSelf - Violin, Mandolin, Percussion, Guitar | Self - Violin, Mandolin, Percussion, Guitar |
| CCory ChurkoSelf - Violin, Mandolin, Guitar, Backing Vocals | Self - Violin, Mandolin, Guitar, Backing Vocals |
 Andy CichonSelf - Bass | Self - Bass |
| AAllison CornellSelf - Violin, Keyboards, Mandolin | Self - Violin, Keyboards, Mandolin |
| HHardy HemphillSelf - Keyboards, Percussion | Self - Keyboards, Percussion |
| MMarc MullerSelf - Guitars | Self - Guitars |
| RRandy WallerSelf - Guitars | Self - Guitars |