He flew from Canada, where he had cut short his attendance at the Group of Seven (G-7) summit.
Kim smiled as he took a selfie with Singapore's Foreign Minister Vivian Balakrishnan at the scenic waterfront Gardens by the Bay.
It was Kim's only foray on Monday outside of the St. Regis hotel, where he's been staying since his arrival a day earlier.
Instead of flying the Pyongyang-Shanghai-Singapore route that takes around six-and-a-half hours but passes over sea, Kim Jong-un flew via Beijing, which took around 10 hours.
"As you know, we've got a very interesting meeting tomorrow", Trump told Singapore Prime Minister Lee Hwien Loong on Monday.
He thanked Singapore's organisation of the summit as if it was "their own family affair".
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The Republic is no stranger to hosting historic summits.
Though the country's nuclear program has dominated headlines due to fears the regime may create a weapon capable of striking the continental US, its team of hackers has been behind some of the bigger cyberattacks in recent years.
There is also an analysis that Pyongyang has intentionally revealed the charter of a Chinese airplane to display a close bilateral relationship in the face of worldwide sanctions led by the U.S.
Trump had called Kim "Little Rocket Man" and threatened to unleash "fire and fury like the world has never seen" on North Korea as it conducted several ballistic missile tests in defiance of worldwide warnings. "I'll give whatever support is needed to my friends, President Trump and Marshall Kim Jong Un", he wrote.
Just to refresh the national memory, an American college student recently died after being subjected to brutal treatment in a North Korean prison, one of hundreds of thousands to suffer violence and abuse by the family-run dictatorship.
Dozens of reporters and cameramen mobbed North Korean chief negotiator Choe Son Hui as she left the hotel amid pushing and shoving.
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Mr Lee is slated to meet Mr Trump today at the Istana.
But last month, Trump abruptly cancelled the Singapore summit, citing the "tremendous anger and open hostility" by Pyongyang. "I don't think we're going to see a momentous agreement".
According to FlightRadar24, a website that tracks the flights of various aircraft, thousands of people followed the progress of Kim Jong-un's plane.
Exuding confidence, Trump said he has done relatively little formal preparation.
"The idea is to force North Korea to do a quick and complete denuclearisation and not to drag it out, which will make the United States look like a fool", Zhang said "The problem here is: will Kim accept this?" "Create peace and great prosperity for his land".
Mr Lee, it said, complimented "the bold and admirable decision" by Mr Kim and Mr Trump to come together for the summit.
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Singapore is one of the few countries that have diplomatic relations with both the U.S. and North Korea.