They are likely to discuss the possible resumption of international talks over North Korea's nuclear programme.
North Korea is in talks with Russian gas monopoly Gazprom about a pipeline through its territory to South Korea.
A delegation from the company visited North Korea last month.
The BBC's Lucy Williamson in Seoul says the pipeline would have a far-reaching political and economic impact, and potentially allow North Korea to control a key energy supply to the South.
South Korea's Yonhap news agency says the North Korean leader is expected to visit a dam north of Vladivostock, before holding summit talks with President Medvedev in Siberia on Tuesday.
The agency quotes an unnamed official as saying Mr Kim may also meet Russian Prime Minister Vladimir Putin.
The leader's visit comes amid severe economic hardship and food shortages in North Korea.
On Friday, Moscow announced it was providing 50,000 tons of wheat to Pyongyang.
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