He was transferred to feeder club Apollon Athens in 1996 as a replacement for retired Antonis Minou, signing a five-year professional contract.

After a fight for first team football, eventually Galinovic won out and due to overseas interest, Chalkias was shipped out to English side Portsmouth F.C.

[7] Over the next few matches Chalkias's wild tactics and inconsistency led to some poorly conceded goals, and he was soon dropped and replaced by Jamie Ashdown.

With the signing of Sander Westerveld in July 2005, Chalkias fell even further down the pecking order, and in January 2006 he left Portsmouth by mutual consent, having made only five league appearances for the club.

Chalkias has contributed to the qualification of PAOK the 2010–11 UEFA Champions League third qualifying round, after winning the preliminaries against AEK Athens, Olympiakos and Aris Thessaloniki F.C.

[19] After Greece's lost quarterfinal to Germany on 22 June, a game which Chalkias watched from the bench, he announced his withdrawal from the national team alongside Nikos Liberopoulos.