In the summit in April, the first time one of the ruling North Korean leaders crossed over to South since fighting in the Korean War stopped in 1953, saw both the leaders lay the roadmap for a nuclear-free Korean Peninsula and permanent peace.
Having aides in meetings with adversaries is known as a way of providing the President with protection, as it prevents comments from being misinterpreted.
The White House said Trump would hold a media interview at 4 p.m. before departing Singapore via Paya Lebar Airbase at 7 p.m.
The president is now in Singapore, just hours away from his historic meeting with Kim.
Trump and Kim met in Singapore on Tuesday and reached a short agreement that reaffirmed the North's commitment to "work toward complete denuclearisation of the Korean Peninsula", but provided no details on when Pyongyang would give up nuclear arms or how that might be verified.
Last week, Trump told reporters that Rodman had not been invited to the summit, but praised him as a "nice guy" and great rebounder. Critics fear that Mr Trump is poorly prepared for the negotiations - while others say Mr Trump's quickfire approach has already produced results - including North Korea saying it is willing to consider denuclearising. As they entered, Trump injected some levity to the day's extraordinary events, saying: "Getting a good picture everybody?"More news: Trump vents anger on North Atlantic Treaty Organisation allies, European Union and Canada's Trudeau
Among those joining the leaders on the USA side were Secretary of State Mike Pompeo, White House chief of staff John Kelly and national security adviser John Bolton. Mr Kim is reported to be flying out even earlier, at 14:00 local time (6pm NZT).
Their first meeting will be at 1pm at the Capella Hotel, a five-star resort on Singapore's Sentosa Island - and a former pirate haunt.
Highlights of the chat will be made available before "Hannity" airs, Fox News said. Pompeo held firm to Trump's position that sanctions will remain in place until North Korea denuclearizes - and said they would even increase if diplomatic discussions did not progress positively.
"It's related to the North Korea-U.S. summit, so if anyone tries to go near the Yalu River, he or she will be accused of anti-regime crimes", the source said, referring to the waterway on the border between the North and China that is a popular route with defectors mainly when it freezes during the winter.
The sides first spoke through intelligence channels, with USA analysts working to determine Kim's true willingness to abandon a nuclear program started by his grandfather and viewed by Pyongyang as a security blanket from outside aggressors. But the 34-year-old North Korean leader also brought a group of trusted lieutenants to Singapore, with at least four high-powered women including his own sister.
Here in futuristic Singapore, however, Kim was able to view the benefits of economic advancement at close range. NPR's Elise Hu joins us now from Singapore.More news: Trudeau supports Trump on North Korea, but won't respond to barbs
Joseph Yun, former USA envoy for North Korea policy, alluded to that when he told a Senate hearing last week that there's a risk of "overloading the agenda" for the summit.
More than 2,500 journalists have convened here, with each leader's every movement tracked carefully.
Trump initially touted the potential for a grand bargain with North Korea to rid itself of a nuclear missile programme that has advanced rapidly to threaten the United States.
The White House said later that discussions with North Korea had moved "more quickly than expected" and Trump would leave Singapore on Tuesday night after the summit, rather than Wednesday, as scheduled earlier.
Hyon is head of North Korea's hugely popular Moranbong girl band, whose members were hand-picked by Kim Jong Un.More news: Raccoon scales office tower, captivating public
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