The White House confirmed Friday a planning is underway.
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Is it a smart diplomatic move, or is President Trump being played by Kim Jong Un? The world will find out when the two leaders sit down together in May. Either way, foreign policy experts said Trump's decision is risky.
"I'm not sure he really understands what he is walking into, or how much risk there is. There is no risk to Kim Jong Un, he has already won," said Cecile She, senior fellow of the Chicago Council on Global Affairs.
Shea, a former U.S. diplomat, said North Korea has longed for a photo op with a sitting U.S. president. She said it will give Kim Jong Un the status of a world leader. But beyond the picture, no one knows his real motivation.
"It is possible that Donald Trump's bellicose verbiage has worked and Kim Jong Un is scared and doesn't want to be destroyed," Shea said.
Shea said it's also possible that North Korean has decided that Trump is easy to manipulate in a way that can meet their own needs.
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In terms of diplomacy the meeting is highly unusual. Experts said whether it's with a U.S. ally or adversary, a face-to-face meeting between the president and a foreign leader does not come until after the United States has negotiated something.
"The meeting is the reward, so both sides know in order for that big important photo-op meeting to happen they have come to agreement on important issues," Shea explained.
For the United States, its goal with North Korea is an agreement on denuclearization and human rights. Illinois Senator Dick Durbin said Trump must be careful.
"All of our negotiations with North Korea have been disappointing. They don't keep their word and we have to go into this skeptical," he said.
Senator Durbin went on to say he hopes the president takes this historic opportunity seriously without any more adolescent tweets. In the meantime, the Korean American Association of Chicago said it is very hopeful the meeting will produce a positive outcome.