Chris started his career at Derby County in England but returned home to sign for Sean Connor at newly promoted Sligo Rovers in December 2005. In 2006 Sligo finished fifth in the Premier Division but at the end of that year manager Connor moved on to Bohemians. in July 2007 Chris followed his former boss, signing for Bohemians in the summer transfer window.

At the end of 2007 Connor left Bohemians and Chris found himself out of favour under new boss Pat Fenlon, leaving the club in the summer transfer window of 2008 to sign for Scottish cub Partick Thistle. He made 2 league appearances for the Firhill club and was released in the winter of 2008, returning to Ireland where he signed for Sean Connor once again at Dundalk.

He made his Dundalk debut on the opening day of the 2009 season and made 31 league appearances for the Lilywhites that season, scoring twelve times.

At the end of the 2009 season he nearly moved to Sligo Rovers but ended up signing for Shamrock Rovers in January 2010. He made his first appearance for the Hoops away to Sporting Fingal on April 5th and was a member of Rovers title winning side that year.

In 2011 Chris won his second League medal as Rovers retained their league crown. He made 23 league appearances and scored three times, adding three more goals in Cup competition including one against Flora Tallinn in the Champions League. Chris played in 10 of Rover's twelve European games during a campaign that took the club into the Group stages of the Europa League.

Chris continued at Rovers under new boss Stephen Kenny in 2012 but in late August it was announced that he was leaving the club and he subsequently went to Scotland where he signed for Dumbarton.