Kushner is hoping to pull off a last-minute foreign policy victory in the region just weeks before his father-in-law President Donald Trump leaves the White House.
The 39-year-old is seeking to end more than three years of a land, air, and sea blockade of Qatar by some Gulf Cooperation Council (GCC) members.
Saudi Arabia, Bahrain, the United Arab Emirates (UAE), and non-GCC member Egypt cut diplomatic and transport links with Qatar in June 2017, accusing Doha of becoming too close to Tehran and sponsoring terrorism.
Qatar has denied the claims and refused to accept a 13-point plan, which demands the Gulf state sever ties with organisations which the blockading countries deem as "terrorists", shut down diplomatic posts in Iran and close a Turkish military base on its soil, to end the siege.
Kushner is expected to meet Saudi Crown Prince Mohammed Bin Salman (MBS) and Qatari Emir Sheikh Tamim Bin Hamad Al Thani during his visit to the region, in efforts to resolve the crisis.
Observers cited by Al Jazeera claim Kushner's meetings are a brazen attempt to provide a satisfying conclusion to the Gulf crisis after Trump failed to quash the diplomatic row in its early days.
Khalil Jahshan, executive director of the Arab Centre Washington DC, was quoted by Al Jazeera as saying: "We cannot forget, when the crisis started, the statements by Mr Trump himself accepted the logic of confronting and isolating Qatar, even though he later changed his mind based on complaints from his own inner circle, and his own secretary of state and his own secretary of defence."
The meetings come as Saudi's position on the crisis appears to have softened.
Foreign Minister Prince Faisal bin Farhan Al Saudi said there could be a route to ending the crisis in the "relatively near future" in October.
Meanwhile, yesterday Saudi Arabia's permanent representative to the United Nations, Abdullah Bin Yahya Al-Mouallimi, said the crisis could end "within 24 hours", in an interview with Russia Today.
Qatar has also seemed keen to end the blockade with Foreign Minister Sheikh Mohammed Bin Abdulrahman Al Thani saying Doha was hopeful it would end "at any moment" in early November.
However, Kushner's trip also comes as his influence in the Middle East is waning because of Trump's pending departure from the White House.
Commentators told Al Jazeera the presidential adviser's trip could be viewed as a personal "swan song" for Kushner, who has been the administration's key diplomat in the region over the last four years.