Kim, who met Singaporean Prime Minister Lee Hsien Loong on Sunday after arriving, thanked him for hosting the event.
Trump flew into Singapore's Paya Lebar Air Base aboard Air Force One, looking to lay the groundwork for a nuclear deal with one of America's most bitter long-time foes, directly following his divisive meeting in Canada with some of Washington's closest allies that further strained global trade ties.
A large limousine with a North Korean flag could then be seen surrounded by other black vehicles with tinted window as it sped through the city's streets to the St Regis Hotel, where China's President Xi Jinping once stayed.
In authoritarian North Korea, where Kim's family has passed on power through three generations, images propagated by state media such as the Korea Central News Agency, the Rodong Sinmun newspaper and Korean Central Television, help build a leader's legitimacy and glorifying his status.
Trump has expressed keenness about his summit with Kim and called it a "one-time opportunity".
He added in addition to using bulletproof vehicles, North Korea's security detail would likely deploy layers of protection surrounding the summit venue and try to divert attention from Kim Jong Un's auto whenever he moves. He's also specifically questioned the need for so many troops in South Korea, asking in 2016, "What are we getting for this?" Trump called the North Korean leader "little rocket man" on Twitter in September.
Trump is dangling before Kim visions of protection, economic investment and even a White House visit, in return for a commitment to abandon his nuclear weapons program.
January 9: North and South Korean officials meet at a border village and agree on North Korea sending athletes and delegates to the Winter Olympics in the South. Hundreds of North Koreans go to the Pyeongchang Games in February, including Kim's sister, who conveys her brother's desire for an inter-Korean summit with South Korea's president.
Sources told CNN that USA officials have established a contingency plan for a potential second day of discussions between Trump and Kim depending on the direction of their planned meeting on June 12. "And again, I say that with hope that maybe something can happen", said the U.S. President.
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As he embarks to Singapore for a summit with North Korea's Supreme Leader, Trump said that it "is going to work out very well". He tweets: "We will both try to make it a very special moment for World Peace!"
"I have the expectation that this (summit) will be very successful".
Another possibility from the summit is a deal to end the Korean War, which North Korea has long demanded, presumably, in part, to get US troops off the Korean Peninsula and, eventually, pave the way for a North Korean-led unified Korea.
More than 1,000 people paid for a photo with the Kim-Trump lookalikes over the weekend.
But, barring a shock last minute development, the historic meeting between the United States and North Korean leaders will go ahead. At the G7 summit in Canada and in the hours afterward, Trump railed against trade practices that he described as unfair and said he'd given USA representatives instructions to rescind an agreement to official communique that outlined a mutual plan to ensure "free, fair, and mutually beneficial trade".
Mr Trump has said it normally takes him about five seconds to figure out whether he will get along with someone.
His last trip was in June 2017 when he gave Kim a copy of Trump's best-selling book, "The Art of the Deal".
Pope Francis has prayed that the summit this week between the US and North Korean leaders succeeds in laying the groundwork for peace.
"I'll give whatever support is needed to my friends, @realDonaldTrump and Marshall Kim Jong Un".
In Canada, the USA president threatened longtime allies over trade practices at a defiant exit press conference before abruptly withdrawing his endorsement of the group's final joint statement and tweeting that host Prime Minister Justin Trudeau was "weak".
The role would be as a "guarantor", Chinese analysts say, not just of progress on the denuclearisation Washington is seeking, but also to ensure what Kim wants most: the safety of his regime.