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Kostas Tsimikas scored the winning spot-kick after Mason Mount saw his effort in sudden death saved by Alisson.
Edouard Mendy prevented Sadio Mane striking the winner after Cesar Azpilicueta had hit the post, only for the Brazil goalkeeper to deny Mason Mount before Kostas Tsimikas struck to seal a 6-5 win.
But Chelsea saw out the early storm and began to ask questions at the other end in a first half that saw Reds star Mohamed Salah limp off injured.
Nothing could split them after 90 minutes and extra time again, with Alisson coming up trumps in the shoot-out as Liverpool won their first FA Cup since 2006.
That pulsating half made way for a tepid period of extra time between exhausted sides that raised themselves for penalties, which ended with red smoke and Liverpool cheers filling the air.
Marcos Alonso’s audacious free-kick hit the bar during a rampant Chelsea start to a topsy-turvy second period, which ended with Luis Diaz and Andrew Robertson striking the post for Liverpool.
Just 76 days after the Reds edged past Thomas Tuchel’s men on penalties following a scoreless Carabao Cup final, Wembley witnessed another gripping clash between these sides that went down to the wire.
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