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Saudi Arabia is visited by millions of pilgrims each year and the visitors are allowed to enter either through the Medina airport or through the Jeddah airport, as there is no airport in Mecca. Depending upon the choices and the priorities of the people, they decide to go to Medina first. One of the reasons is to avoid the hassle and the crowd that is always experienced by them at the Jeddah airport. This makes Medina a good option for the pilgrims to land on.
Masjid e Nabawi is situated in Medina where the sacred resting place of our beloved Holy Prophet Muhammad (PBUH) is. To revive the divine spirit of Islam and for the love of the Messenger (PBUH) of Allah, the pilgrims go to Medina first to say nawafil in Masjid e Nabawi. Saying Salaam to our dearly loved Prophet (SAWW) first, before going to Mecca, has always been practiced by our predecessors for the spiritual dimension involved in it.
An additional rationale behind the visit to Medina first is the liberty from Ihram and the obligatory restrictions that come with it. You can visit Roze e Rasool without wearing Ihram. When you are done with the sacred stopover at Masjid e Nabawi and ready to go to Mecca then you can go to Masjid Meeqat in Medina to enter into Ihram and perform the rituals associated with it.
The religious scholars agree upon some other beliefs based on the Hadith of Holy Prophet (PBUH) and this becomes another reason for most of the people to go to Medina first. It is reported in al-Musnad book of Hadith and al-Mu’jam book of al-Tabarani from Anas in a Marfou’ Hadith (traceable in ascending order of Hadith to Prophet (Sallallahu Alaihi wa Sallam)):
“Whoever performs forty times of prayer in my mosque (the Prophet’s (PBUH) Mosque) with the congregation of the mosque, a statement of being exempt of the Hell-fire and a salvation from its torture will be written to him/her, and he/she is considered free from hypocrisy”.
Another motive to visit Medina first that is sought by most of the pilgrims is the alleviation from tiredness that comes from the travel and the regularity of the busy routine. In Medina, you can get the time enough to make up your heart for the religious sacredness of the rituals that are waiting for you in Mecca. You need to get into that harmony by doing Ibadah and revising the holy practices and for this purpose going to Medina first is a wise choice.
Apart from that, taking a return flight from Medina will save you from any extra road travel that you will have to do from Medina to Jeddah by road if you take a return flight from Jeddah. May Allah guide us right for He is the Glorious one who knows the best!