The meeting comes against the backdrop of a war of words between the political leaderships of the two states over the Gorkhaland agitation.
The talks are significant also because of the issues likely to be taken up, such as recent problems in the movement of commercial vehicles stemming from tighter checks, trade and tourism - sectors where the two states' fortunes are interlinked.
Mamata Banerjee had earlier warned Mr Chamling to not indulge in affairs of Darjeeling and alleged his government of sheltering Gorkha leader Bimal Goring. Sources say one of the prime reasons she wants improved relations with Sikkim is due to its sizable Gorkha population. Taking them into confidence can help her manage the Darjeeling hills better, official sources add.
The relationship soured after the agitation for statehood started in the Darjeeling hills last June and Mr Chamling wrote to Union Home Minister Rajnath Singh backing the Gorkhaland demand.
Some Morcha workers were arrested in the raid. But Sikkim police alleged their Bengal counterparts did not inform them about the searches and lodged counter cases against Bengal police.
The Darjeeling turmoil and strained relation between West Bengal and Sikkim had also resulted in heavy losses to tourism and transport sector in the last financial year.
Get the latest election news, live updates and election schedule for Lok Sabha Elections 2019 on ndtv.com/elections. Like us on Facebook or follow us on Twitter and Instagram for updates from each of the 543 parliamentary seats for the 2019 Indian general elections.