Trump, who had the basketballer on his Celebrity Apprentice show twice, has recently called Kim a "smart cookie" and has said he would be "honored" to meet him.
"I'm just here to see some friends and have a good time", he said.
Dennis Rodman has made several trips to the mysterious country as he claims the tyrannical leader is a "good kid" - but what else is he famous for?
Rodman's trip to North Korea is at least his fifth time to the reclusive nation. While the U.S.is aware of the current visit, Rodman is acting as a private citizen. North Korea is expecting another visit by Rodman on Tuesda. "They've been looking at ways to do that", Pinkston said.
The former basketball star has received the red-carpet treatment on four past trips since 2013, but has been roundly criticised for visiting during a time of high tensions between the U.S. and North Korea over its weapons programs.
Americans are regarded as enemies in North Korea because the two countries never signed a peace treaty to formally end the 1950-53 Korean War.
It is not clear whether Rodman, who once dated U.S. singer Madonna and was married to United States model and actress Carmen Electra, will be meeting Kim Jong Un during the current trip or what its exact goal is.
Any visit to North Korea by a high-profile American is a political minefield, and Mr Rodman has been criticised for failing to use his influence on leaders who are otherwise isolated diplomatically from the rest of the world. We wish him well. "My goal is to go over there and try to see if I can keep bringing sports to North Korea", the former Chicago Bulls forward told CNN. He was sentenced to 15 years in prison with hard labor.
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"Headed back to North Korea". But efforts to convince North Korea to release the men now held have not been successful so far. On the same trip, he suggested that an American missionary was at fault for his own imprisonment in North Korea, remarks for which he later apologized. Rodman returned the following year and organized a game between formerly professional American basketball players and North Korean players in order to celebrate Jong-Un's 30th birthday. The trip quickly turned into a debacle, with sponsors dropping some of the players, who went on CNN to try to explain why they were there.
At the start of the exhibition game, Rodman sang "Happy Birthday" to Kim, who was seated in the arena, and bowed deeply as the North Korean players clapped. The trip was captured in the documentary Big Bang in Pyongyang.
Rodman has met Kim on some but not all of his previous trips.
People familiar with the basketballer's trip preparations said that Rodman was due to travel to Pyongyang last month but the trip was delayed.
A foreign ministry official in Pyongyang confirmed that Mr Rodman was expected to arrive Tuesday but could not provide details.
Some of Rodman's previous interactions with Trump had been captured on television. Rodman was a cast member on two seasons of Trump's "Celebrity Apprentice". But Trump fired Rodman for spelling his wife Melania's name wrong.
"Dennis is not a stupid guy", Trump said. "Dennis, you're fired" Trump told the basketballer, who was wearing his trademark sunglasses and adorned with piercings.
Former NBA basketball player Dennis Rodman, center, arrives at Beijing Capital International Airport in Beijing, Tuesday, June 13, 2017.
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