Political timeline:

1994 - He was elected as Member Panchayat from Village Ramgarh, District Kapurthala.
1997 - He joined the Youth congress and was appointed as vice president of Punjab Youth Congress.
1999 - Punjab Pradesh Congress Committee appointed him as secretary of their organisation.
2005 - He was appointed president of Kapurthala district's Congress committee (2005 to 2010).
2006 - He became elected director of Central Cooperative Bank, Kapurthala.
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.
2009 - He was appointed as Punjab Congress Spokesperson and was reappointed in 2013, (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).
2015 - on 25 December Khaira announced his resignation from Congress party and declared his unification with the Aam Aadmi Party.
2017 - on 11 March, Khaira won the Member of Legislative Assembly elections second time after failing in 2012 in his constituency of Bholath, however this time acting under the Aam Aadmi Party.
2018 - Suspended from AAP for anti party activities
2018 - Formed Punjab Democratic Alliance
2019 - on 6 January, Khaira left Aam Aadmi Party
2019 - On 8 January 2019, he formed a new political party, Punjab Ekta Party.
2019 - On 16 March 2019, Punjab Democratic Alliance announced his candidacy from Bathinda parliamentary constituency.
2019 - On 25 April 2019 he resigned from Punjab Legislative Assembly.
2019 - On 23 May 2019, he lost from the Bathinda Lok Sabha Constituency.
2022 - on 10 March,Khaira won the Member of Legislative Assembly election third time from Bholath, this time as an Indian National Congress candidate.