The veteran Italian defender, who won nine Serie A titles at Juventus and Euro 2020, now plays for Los Angeles FC in the MLS.
LAFC welcomed Messi's new club, Inter Miami, to the BMO Stadium on Sunday night to give Californian fans their first chance to see the 2022 World Cup winner in action.
It was also a chance for Chiellini to get a picture that will live long in the memory of him and his family following.
Despite his side losing 3-1, Chiellini was in good spirits and was quick to grab Messi for a picture opportunity.
Messi is no stranger to posing for photos with supporters and did so once again as the 39-year-old crouched down to take the snap.
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The pair them embraced following the heartwarming incident, with fans loving the wholesome content.
Replying to a video posted by ESPN, one user said: "I see nothing but two legends."
Another messaged: "Nothing but two great Legends and two two really good-hearted people."
A third added: "Look at his kids, so happy!"
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This fan then simply stated: "His kids reaction is priceless."
However it wasn't a completely positive reception for Messi in the City of Angels with the Barcelona icon booed by the home supporters.
Meanwhile Hollywood A-listers such as Leonardo Di Caprio and Selena Gomez watched on, along with Prince Harry who was cheering on his local club.
However it was the 36-year-old who had the last laugh on the night.
While he didn't get on the scoresheet on the night, Messi did provide two assists in the 3-1 win to lift Inter off the bottom of the Eastern Conference table.