The Argentinian pontiff took off from Rome's Fiumicino airport shortly before 7am GMT en route to Havana.
Francis and Kirill are set to sign a joint declaration on the contemporary persecution of Christians in places such as Iraq and Syria, at around 9.30pm.
'We are brothers,' Pope Francis said, as the pair embraced.
'Now things are easier,' Kirill agreed. 'This is the will of God,' the pope said.
The meeting on neutral ground has been decades in the planning, with the final obstacles finally swept away by a combination of the Pope's determination that it should happen and the Russian church's feeling that events in the Middle East have made Christian unity much more urgent.
The rapprochement with the Orthodox wing of Christianity is in line with the pontiff's drive to make the Vatican a more active player in international diplomacy.
'I just wanted to embrace my Orthodox brothers,' he said in an interview this week.
But he also framed the encounter in a broader context of engaging Russia, saying Moscow could be an important partner for peace in the world.
Francis has twice received President Vladimir Putin at the Vatican since he was elected pope in 2013.
'In the background there is a third player (Putin),' Vatican expert Marco Politi wrote in a blog on the historic encounter.
'It would be naive to believe the sudden availability of the patriarch is unrelated to the geopolitical situation Russia finds itself in at the moment,' he argued, in a reference to Russia's intervention in Syria.
A spokesman for the Orthodox church in Moscow said he could '100 per cent guarantee' that there was no political agenda behind the two religious leaders' meeting.
Patriarch Kirill gave a supportive message to the Cuban leader Raul Castro when they met earlier this evening, ahead of Kirill's meeting with the pope.
Russian news agencies reported from Havana that Patriarch Kirill told Castro that the Cuban people 'have proved their right to live in the way they believe is fit'.
Russia's state RIA Novosti news agency quoted him as saying that 'heroism is a spiritual concept that cannot be learned from books. It derives from man's spiritual life'
Alexander Volkov said he hoped the meeting would open the door to 'new prospects of mutual cooperation', but emphasised that reunification of the Eastern and Western churches was not on the agenda.
Despite the breakthrough of a face-to-face meeting, Vatican-Orthodox relations remain strained.
The issues that caused the schism in the first place are unresolved and there are tensions over the perceived evangelism of the Catholic Church in Eastern Europe.
Then there is the fallout from the conflict in Ukraine, which has pitted Ukrainian Catholics loyal to Rome against separatists who are mostly Russian Orthodox.
Francis's arrival in Mexico this evening is set to be a luminous affair, with hundreds of thousands of well-wishers expected to line the 12-mile route from the airport to the Vatican ambassador's residence in Mexico City.
The plan is for believers to light up the road the Popemobile will travel with their mobile phones or hand-held torches, creating what local organiser Roberto Delgado described as a 'wall of light and prayer'.
Francis will spend his nights in Mexico at the ambassador's residence in the capital, but will make a series of trips to outlying states stricken by violence and poverty.
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