During the pursuit of creating music, he attended university and graduated with a Bachelor of Education degree. He currently works as an Academic Counsellor for the Saskatchewan Indian Federated College (Saskatoon Campus). He and his family created Falcon's Dream Records in 1997, an independent label that is marketing his music and other First Nations musicians.

Chester released his debut album Freedom in June, 1996 and has since sold over five thousand units. Several months after its release Chester was nominated for a Canadian JUNO award. Through Falcon's Dream, Chester has established distribution agreements with Festival Distribution (Canada), Sound of America Records (SOAR, USA). His CDs are now available in most major retail outlets in North America.

He released his second album Falling Down through Falcon's Dream Records in March, 1999. Chester and producer Michelle Garuik, recorded 12 songs at Grind Recording Studio in Pense, Saskatchewan. This album received several awards which are; 2000 JUNO Award, first annual Prairie Music Award, first annual Canadian Aboriginal Music Award and a First Nations Award.

Chester Knight and The Wind's live performances are electric. They toured Canada's biggest music festivals the last two years. The band rocked main stages before thousands at the Harbourfront Centre, Toronto (twice in two years) and the major folk music Festivals of Vancouver, Edmonton, Regina and Winnipeg.

Chester wrote songs for the highly acclaimed play "Lady of Silences" written and directed by Floyd Favel and recently performed at the Globe Theatre in Regina. The entire music from Falling Down was incorporated into another play called "Truth Hurts", produced by the Saskatchewan Native Theatre Company. Blue Hills Production in Saskatoon, produced a documentary of this play entitled "Circle of Voices," using Chester's music for the sound track. Two music videos were produced, one with CBC and another for Much Music. A CBC Prairie Roadhouse Special featuring Chester was nominated for an award at the 1997 Dreamspeaker Festival. He also created a theme song for a film documentary "Voices in the Wind," that was aired on BBS television. Chester appeared on a 1997 CBC Canada Day Special that was aired nationally. The song "Love Me Strong" from Freedom was included in a compilation album that has just been released in the USA through an agreement between SOAR and Falcon's Dream. Recently through another agreement between SOAR and Falcon's Dream, the CD titled Falling Down was changed to Windfall and this was released in May, 2000 in the USA.