The retired Italian was the latest guest on The Overlap on Tour, where he spoke about his glittering playing career and the times when he almost ended up playing in England.
The discussion soon turned to one of the Euro 2020 winner's teammates during his time at Juventus.
Chiellini, one of the greatest defenders in modern football, was presented with the difficult task of marking Ronaldo six times during the Portuguese superstar's time at Real Madrid.
In those six games, Ronaldo found the back of the net every time and ultimately scored nine goals against Chiellini.
Luckily for the Italian, Ronaldo switched from foe to friend when he moved from Madrid to Juventus for £105million in July 2018, with the pair being teammates for three years, playing 55 games together.
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They won five titles while being on the same team, including back-to-back Serie A crowns.
Training and playing alongside Ronaldo proved to be an eye-opening experience for Chiellini, even if, by his own admission, both were no longer in their prime.
"Well, Ronaldo, when you are losing, he had the balls, no matter what, to try to win," Chiellini said.
"Shoot from everywhere in order to lead the team to win. And it is not easy to do for a lot of players.
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"I loved to play with him because working with him and looking at him every day, with little details, is very nice.
"I was 35 and he was 34, and we weren't obviously in our prime. But it was very funny to play with him. And look how big is his personality."
Chiellini was then asked the age-old question that has dogged modern football: Messi or Ronaldo?
The Italian largely swerved the debate, but provided a telling answer that hints at where he stands on the matter.
"We cannot say for me, who is better, Messi or Cristiano," Chiellini said.
"But if I have to pick one, for a final, Cristiano."
Chiellini added: "I love to play with Cristiano. And I saw when the game is more difficult, he raises his level of performance."
Across Ronaldo's illustrious club and international career he has been on the winning side of a final 24 times.
This included the Coppa Italia in the 2020/21 campaign.
Ronaldo started the match alongside Chiellini against Atalanta and helped the Old Lady to a 2-1 victory.
He didn't score but provided a vital contribution in the semi-final with a double against Inter Milan.
The superstar striker was also involved in two Italian Super Cup finals while with Juventus and claimed victory in both of them as well.
In the 2-0 win over Napoli in 2020, he scored, while he also bagged the only goal of the game in 2019 when Juventus beat their old rivals AC Milan.
However, the Portuguese icon was unable to add to his tally in August when Al-Nassr lost the Saudi Super Cup final to fierce rivals Al-Hilal.
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Ronaldo scored his side's only goal as they lost 4-1.
But the 39-year-old did not stick around to receive his runner-up medal as he opted to make a swift exit down the tunnel and back to the dressing room.