Till these flairs seen, helicopter in that square ring

from XV – This Plane Lyrics on Rap Genius

Whether it’s a helicopter or airplane there is always someone near the landing spot who lets the pilot know that it is clear and safe to land and has flares in his hands.

Flair is also a play on homonyms.
-Flare as in alert a landing
-Flair as in a natural talent, or distinctive style.

XV is showing his talent and riding in helicopters (which are very expensive) around the world.

Helicopters tend to land on a helipad and sometimes had square rings. Notice the Square around the ‘H’

Square is also refers to XV himself as someone who is different from the norm.

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