Chalkias started his career in thePanathinaikos youth academy in the 1994–95 double winning team. He was transferred to feeder clubApollon Athens in 1996 as a replacement for retiredAntonis Minou, signing a five-year professional contract.[3] His solid performances helped Apollon avoid relegation fromAlpha Ethniki[4] and made him return to Panathinaikos two years later, in 1998.[5] However, he did not get any playing time at Panathinaikos by his head coachVasilis Daniil and in January 1999 he was re-sent to Apollon on loan for six months.[4][6] After his return, he was forced to play third keeper to the legendaryJozef Wandzik and Greek legendAntonis Nikopolidis. He made a total of 25 starts over the next three years between 1998 and 2001 for Panathinaikos and was transferred for two seasons toIraklis before good performances led to a return to Panathinaikos in the 2003–04 season. After playing second fiddle again to Nikopolidis during most of the 2003–04 season, he was allowed back into the first team after a dispute Nikopolidis had with management.
At the end of the 2003–04 season, Nikopolidis was let out on a free transfer to bitter rivals,Olympiakos, and a new keeper was bought,Mario Galinovic. After a fight for first team football, eventually Galinovic won out and due to overseas interest, Chalkias was shipped out to English sidePortsmouth F.C. in January 2005, making his debut in theFA Cup fourth round tie away at fierce rivalsSouthampton.[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 byJamie Ashdown. With the signing ofSander 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.[8] Shortly after his release from Portsmouth he joinedSegunda División sideReal Murcia.[9]
Chalkias was bought in the summer transfer window of 2006 byAris Thessaloniki, who were then newly promoted to theGreek Superleague.[10] After his transfer to Aris, Chalkias regained some of the form that he showed during his bright run in the first team for Panathinaikos and after an exceptional season, he was recalled tο the national team and gained a starting spot overAntonis Nikopolidis after the latter's poor performance earlier in aEuro 2008 qualifying match againstTurkey.[11]
Chalkias left Aris in late May 2008 after his contract was due to run out[12] and on 28 May 2008 he agreed to sign a two-year contract for rivalsPAOK,[13] thus becoming the third player to have played for the all three major clubs ofThessaloniki (Iraklis, Aris, PAOK) following Apostolos Tsourelas andStefanos Borbokis.[12]
In the 2009–10 season he reached the second position with PAOK and the semifinal of the Greek cup. In January 2010 he renewed his contract with PAOK for two more years. Chalkias has contributed to the qualification of PAOK the2010–11 UEFA Champions League third qualifying round, after winning the preliminaries againstAEK Athens,Olympiakos andAris Thessaloniki F.C.
On 22 September 2012, Chalkias announced his retirement from football.[14]
After four years of inactivity, he returned to the football for the Greek teamPanachaiki.[15] He was the last player from the legendaryEuro 2004-winningGreece team to retire from professional football.
Chalkias made his debut on 10 November 2001, in a friendly 4–2 home win against Estonia, as he replacedAntonis Nikopolidis at half time.[16] In the summer 2004 he was part of the squad which wonEuro 2004, although he was only the reserve 'keeper.[8]Otto Rehhagel called him also for the qualification of Euro 2008. Chalkias played as the first goalkeeper for theGreece national team during most of the qualification for the World Cup 2010, after the retirement of the legendary goalkeeperAntonis Nikopolidis and he is the only goalkeeper from theEuro 2004.[17]
InEuro 2012 Chalkias was the oldest player at the tournament at 38 years of age and one of just three players remaining from the victorious 2004 Greek squad.[18] On 12 June 2012, he started the second group stage match againstCzech Republic – at the 21st minute of the match, and having conceded two goals in 6 minutes, he was substituted withMichalis Sifakis due to injury.[19] After Greece's lost quarterfinal toGermany on 22 June, a game which Chalkias watched from the bench, he announced his withdrawal from the national team alongsideNikos Liberopoulos.[20]
^Αγώνες Εθνικής Ανδρών του 2010 (in Greek). Ελληνική Ποδοσφαιρική Ομοσπονδία (Greek Football Federation). Archived fromthe original on 26 May 2011. Retrieved2 February 2011.