He began his career with Hibernian and made over 40 appearances in the Scottish Premier League before being released in 2009. Chisholm then had short spells with Shamrock Rovers and Darlington before signing for Arbroath. He played for Dundee during the 2011-2012 season.
Chisholm started his career with Hibernian, where he was fast-tracked by manager John Collins to join the first-team squad for a winter training camp in Marbella during the 2006-2007 season, having previously been with the under-19 squad.
He subsequently made his debut later in the season and was given a two-year contract. Manager Mixu Paatelainen said that Chisholm "is a bit of a leader, he talks, he organises".
Paatelainen was replaced by John Hughes as Hibs manager during the 2009 close season, and one of his first decisions was to release Chisholm. Chisholm then made a guest appearance for Shamrock Rovers in a friendly against Newcastle on 11 July 2009 at the Tallaght Stadium, and signed for the club on 13 August, until the end of the League of Ireland season.
He scored for Rovers in a FAI Cup match against Sporting Fingal, his only goal for the club
Chisholm signed for Darlington on 2 March 2010, and made his debut the same day against Portuguese Vale. He was released by the club following their relegation from Football League Two, along with 13 other players. Chisholm signed for Arbroath in October 2010.
He joined the club at the same time as Patrick Deane, another former Hibernian youth product.
He signed for Dundee on 21 June 2011. Chisholm was released by Dundee at the end of the 2011-2012 season.
He then moved to Bulgaria, signing for second division club Shumen 2010. After half a season in Bulgaria, Chisholm returned to Arbroath.
He was made captain of the team following the departures of Stuart Malcolm and Mark Baxter to Forfar.
Chisholm signed for Junior side Hurlford United in July 2014.