The retired basketball player and NBA Hall-of-Famer was spotted at Beijing Capital International Airport Tuesday, though he wasn't too responsive to questions from the press.
Rodman reportedly said he was hoping to do "something that's pretty positive" on the trip.
North Korean officials confirmed that Rodman was expected to arrive in Pyongyang later today.
Rodman announced his trip on Twitter, where he thanked PotCoin.com for sponsoring his mission. (A quick look of PotCoin's website reveals that it's a cryptocurrency network and banking platform for the marijuana industry).
"I'll discuss when I return," the eccentric athlete wrote in the rather cryptic tweet.
He also posted an accompanying video on Youtube announcing the trip (VPN on):
It's not clear what the purpose of Rodman's trip is, and a senior US State Department official told CNN that he was not visiting "in any official capacity."
This isn't Rodman's first trip to North Korea — he's visited the country at least four times, with three of those trips taking place between 2013 and 2014. Rodman, who is one of just a handful of American citizens to meet the North Korean dictator, has claimed his trips are "basketball diplomacy."
His most recent visit was in January 2014, when he brought along several former NBA players for an exhibition game as a birthday present for Kim. During the trip, he was filmed leading a round of "Happy Birthday" for Kim, who he had previously referred to as "a very good guy."
But as you may recall, the trip quickly turned into a bit of a debacle after Rodman's outburst during a live interview from Pyongyang with CNN. Rodman, who had defended the trip as "a great idea for the world," appeared outraged after a question about then-detained American citizen Kenneth Bae.
The controversial interview drew criticism from activists, who said that Rodman was ignorant of North Korean human rights issues.
Rodman later apologized, saying he was "stressed out" and "had been drinking" around the time of the interview. He also told ESPN that he would "never go back" to North Korea and was sorry he ever went.
Before entering the political world, Donald Trump praised one of Rodman's trips as being "smart."
Accusing Rodman of being "either drunk or on drugs (delusional)," Trump said he was glad to have fired Rodman during Season Six of his hit reality TV show, Celebrity Apprentice. In case you're wondering why Rodman was fired, it was because he misspelled Melania's name on a birthday card. (VPN on):
When asked today if he had spoken to Trump about the trip, Rodman replied, "I'm pretty sure he's happy at the fact that I'm over here trying to accomplish something that we both need."
Rodman's visit comes during heightened tensions between North Korea and the US. Just last month, the DPRK claimed that US and South Korean intelligence agencies attempted to assassinate Kim Jong Un. Four American citizens are also currently being detained in North Korean prisons.
And despite attempts by Trump to work together with China on the issue, the DPRK has already fired 16 missiles this year, including one just last week.