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 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).

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.

Over three and a half years after her last live show, Shania performed a series of three outdoor concerts in Europe and North America in July 2003 to promote her fourth studio album Up!

The singer scheduled the trek primarily because of her prolonged absence from live performances and to ensure playing a concert in the United States prior to her Up!

"[1] She conceptualized the shows to consist mainly of uptempo numbers and to be almost void of ballads to "spend the night rocking" and maintain an energized spirit.

The singer then headed to Chicago, Illinois to perform a free outdoor concert on July 27, 2003, held at the Hutchinson Field in the south-side of Grant Park.

[4] Meanwhile, the National Broadcasting Company (NBC) was seeking an artist to host a prime time television music special, and contacted Twain to discuss the possibilities of filming the concert in Chicago.

NBC executives sought Twain for the special because they believed her lengthy career and crossover history would translate into more viewers.

[1] Prior to performing at Grant Park, Twain spent a week in Chicago to film behind-the-scenes footage that would be used for the television special.

She visited landmarks and attended local events, such as a Chicago Cubs game where she tossed the first pitch and sang "Take Me Out to the Ballgame" for the audience.

The singer also took a riverboat trip and visited outposts of her favorite charity Kids Cafés, a program specialized to feed children in America.

[8] The show commenced with Shania, who was costumed by a "Body Glove" top and black cargo pants, arriving from the back of the stage to perform "Man!

In the succeeding segment, Shania donned a tan, multi-patterned halter top with the words "True Love" spelled on the front and black, sequined wide leg trousers.

[10] The singer returned to the stage for the third and final segment, wearing a black, long-sleeve top with an American flag imprinted in the center and denim capri pants.

He believed that the video would make the singer's naysayers realize Shania's vocal talents and ability to entertainment and interact with a crowd.

"[11] Bobby Reed of the Chicago Sun Times believed Shania failed to give insight into her identity or personality, noting she never mentioned her relocation to Switzerland or her then-new son, Eja.

[19] Mark Guarino of Arlington Heights' Daily Herald believed the concert was evidently tailored for television and that Shania played the proper host.

He continued, "As the night wore on, Shania tried different ways, with varying degrees of success, to make the magnitude of such a large event work for the small screen.

Live in Chicago was certified platinum by the Recording Industry Association of America (RIAA) for shipments of 100,000 copies in the United States.

[26] In Brazil, the video was certified gold by the Associação Brasileira dos Produtores de Discos (ABPD) for the sale of 15,000 copies.