It began on September 25, 2003, in Hamilton, Ontario and finished on July 10, 2004, in Sunrise, Florida.

According to Billboard magazine, the tour grossed $87 million from 96 reported shows between 2003 and 2004.

The performance was shown on NBC and CBC in August 2003, with the DVD released in November 2003.

The performances of "She's Not Just a Pretty Face" and "It Only Hurts When I'm Breathing" were later used as music videos to promote the aforementioned singles.

Live in Chicago was certified platinum by the RIAA for shipments of over 500,000 copies in the United States.