Sokratis Papastathopoulos's injury-time equaliser for Greece had cancelled out Bryan Ruiz's side-footed opener and sent the game into extra time.
Costa Rica, down to 10 men for almost an hour after Oscar Duarte's dismissal, scored their first four spot-kicks.
Theofanis Gekas missed for Greece, and Michael Umana settled the tie.
It means the Central American side - surprise qualifiers from a group containing England, Italy and Uruguay - go through to face the Netherlands on Saturday for a place in the semi-finals as their unlikely run at the World Cup continues.
The last-ditch equaliser and the penalty shootout added belated drama to what had been a less than enthralling encounter at times.
Dimitris Salpingidis had the best chance of a turgid first half but his close-range volley from a fine Jose Holebas cross was saved by the legs of Costa Rica's Keylor Navas - the first of several crucial interventions by the Levante keeper.
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