He has also dangled the prospect of Kim Jong Un visiting Washington if the meeting goes well.
As far as we know, his despot father only traveled out of the country by train, and rarely at that, because of fears of assassination. He also suggested South Korea, China and Japan would be prepared to help the North's economy. Glor will also lead Special Reports for coverage on the summit, and contribute to CBSN, CBS News' 24/7 streaming news service. In 2005, North Korea was testing long-range missiles while promising to do its utmost to denuclearise the Korean peninsula. But amid the curiosity is an even more fundamental question: Why is he taking this risk at all?
Donald Trump issued a warning to Kim Jong-un that he was offering a "one shot" deal for North Korea to denuclearise and re-enter the global community.
The South China Morning Post on Friday reported, citing a South Korean military source, that Beijing might support the trip by sending its fighter jets to trail Kim Jong Un's aircraft en route to Singapore.
"The president on Saturday said that he has a "clear objective" heading into the Singapore summit, but that 'it's going to be something that will always be spur of the moment" because Kim has "never been tested".
There are clues that something unprecedented is indeed happening - no US president has met with a North Korea leader, after all. The law imposes a financial ban and asset freezes on the government and its component parts, and the Workers Party of Korea, of which Kim is the chairman. How can such rallies take place there?
The short answer might be that, despite his safety worries, Kim could end up getting much more out of this summit than he will have to give up.
Theresa May "too weak" to stand up to Trump, says Corbyn
Trump won the presidency with the help of farm-heavy states like Pennsylvania, Wisconsin, Ohio, and Indiana. He has echoed the administration's position that America has gotten the short end of the stick from China.
Trump then launched into a rambling monologue in which he appeared to compare meeting the North Korean leader with deciding if he might have a schoolyard crush on someone.
Before he left Donald Trump said he would know in the first minute if Mr Kim was serious about the talks. I'm sure the North Koreans would sign up for that.
At the end of the presser, he said that the minimum he was hoping for was a relationship and a dialogue. At the root of this desire lies their central concern: "regime survival", he wrote.
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U.S. policy since the Obama Administration was that Washington would not negotiate with North Korea unless the Pyongyang government agreed beforehand the topic would be denuclearisation. And when they blow up at a presidential level, Kristof points out, it's hard to put the pieces back together. "So it's a one-time, it's a one-time shot, and I think it's going to work out very well", Trump said.
His earlier visits to North Korea included a basketball game that he organized, an event chronicled in the documentary film "Big Bang in Pyongyang", which featured Rodman singing "Happy Birthday" to Kim, as well as scenes of inebriated and erratic behavior by the basketball Hall of Famer.
"Kim confronts rising expectations from within at the same time that he contends with ever-tightening sanctions from overseas", Haas wrote.