He got political legacy from his father Sukhjinder Singh Khaira, a stalwart Akali leader.

[6] In 2007 he was elected as Member of Legislative Assembly from Bholath till 2012 under the Congress party, Kapurthala, Punjab after two failed attempts in 1997 and 2002.

He later resigned in 2014 from the post, owning moral responsibility for the "poor performance" of the party in the 2014 Lok Sabha polls in the state.

He formed Punjab Democratic Alliance[11] On 6 January 2019, Khaira left Aam Aadmi Party.

[12] On 16 March 2019, Punjab Democratic Alliance announced his candidacy from Bathinda parliamentary constituency.

[18][19] In 2024 general elections, Khaira contested from Sangrur Lok Sabha seat where he was defeated by Gurmeet Singh Meet Hayer of Aam Aadmi Party by a margin of 172560 votes.