The last time Rodman visited the country was in January 2014, when he and a group of former basketball players participated in an worldwide basketball exhibition which was marked as a birthday gift for Kim Jong Un, who is a big time basketball fan.
Rodman was spotted by reporters at Beijing International Airport, China but refused to respond to questions put to him.
It's not known why Rodman is making the trip to Pyongyang now, when the relationship between North Korea and the U.S.is at a low point.
Rodman is one of the only Americans to have met Kim Jong Un and will arrive at a time of high tension between North Korea and the U.S. as Pyongyang seeks to expand its nuclear weapons program.
Rodman, 56, nicknamed "The Worm" during his playing career and known for his tattoos, body piercings and multi-colored hair, is considered one of the best defensive players and rebounders in National Basketball Association history. This will be the fifth time he will be visiting the North, the most recent coming in 2014. But Rodman apologized, and Bae later thanked the basketball star after he was released, saying the attention Rodman had brought to his case was helpful.
The fact that Rodman was going for such a short period of time raised expectations that he might be going to free the four Americans being held by North Korea.
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Rodman also visited North Korea in January 2014, just weeks after Kim made a stunningly violent move to strengthen his grip on power - executing his uncle and onetime No. 2 Jang Song Thaek for alleged treason. Mr Rodman has called him his "friend for life".
His comments drew criticism at that time, but Bae said in his interview with CNN in 2016 that he is grateful to Rodman for being a "catalyst" for his release from the repressive regime.
In 2014, Rodman arranged a basketball game with other former NBA players and North Koreans and regaled leader Kim Jong Un with a rendition of "Happy Birthday". North Korea is developing its nuclear weapons and missiles at an alarming pace with the stated goal of launching an intercontinental ballistic missile capable of hitting the US mainland.
A foreign ministry official who spoke to the AP in Pyongyang confirmed Rodman was expected to arrive on Tuesday but could not provide details. He was heavily criticized in the U.S. for not bringing up the case of Kenneth Bae, an American imprisoned on charges of "hostile acts" who spent 735 days in North Korean custody before being released in 2014.
It would be Rodman's first visit to the country since President Donald Trump took office.
Former NBA basketball player Dennis Rodman, left, gestures to photographers as he prepares to go through immigration at Beijing Capital International Airport in Beijing, Tuesday, June 13, 2017.