Rodman's North Korea visits over the years have fueled speculation that he could somehow facilitate a diplomatic breakthrough between Pyongyang and Washington. A senior US official said the State Department was aware Rodman was scheduled to travel to the North, but stressed he would not be there in any official capacity, according to CNN.
Trump called Rodman "smart" for his 2013 trip to North Korea, Politico reported at the time.
North Korea has touted its drone program in recent years, and South Korean officials believe its military has about 300 drones.
The objective of Rodman's visit remains unclear, though it comes amid heightened tensions between the United States and North Korea over Pyongyang's nuclear program.
When Rodman visited the North in February 2013 with the Harlem Globetrotters, an exhibition basketball team, Kim was said to have personally gifted him with a present that said, "For our friendship".
Rodman, who has made several trips to the country, sported a black T-shirt advertising a marijuana cybercurrency as he headed toward immigration at Beijing airport, from where he is expected to fly to Pyongyang, the North Korean capital.
Rodman was also spotted at the Beijing International Airport on Monday night where he refused to answer questions about his visit.
"This visit will be judged not by who he takes with him but by who, if anyone, he brings back", said Scott Snyder, a Korea expert at the Council on Foreign Relations. The other three citizens being held are Tony Kim, Otto Warmbler, and Kim Dong Chul.
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.
The visit, the goal of which remained unclear, would be Rodman's latest to the nuclear-armed nation. 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. Most recently in 2014 he attracted a deluge of criticism after being filmed singing happy birthday to his "friend for life", leader Kim Jong-Un.
It came amid heightened tensions between Washington and Pyongyang, which is now detaining four Americans. He and his friends, Terwilliger and Volo, are the only Americans known to have met Kim.
The former National Basketball Association star teamed up with online betting firm Paddy Power for a series of trips to the isolated nation in 2013.
Some of Rodman's previous interactions with Trump had been captured on television.
The former basketball star also has a personal relationship with current U.S. President Donald Trump, having appeared on the reality TV show "Celebrity Apprentice", which was hosted by Trump before he was elected. But Trump fired Rodman for spelling his wife Melania's name wrong. No, no, no, you tell me, you tell me. The value of PotCoin surged following Rodman's announcement early Tuesday.