An inflight connection system for aircraft having at least one wing with a wingtip includes, for each aircraft, a primary connector selectively extendable from the wingtip, an alignment connector selectively extendable from the wingtip and a male and female connector assembly disposed proximate the wingtip. The primary connectors extend a greater distance from the wingtips than the alignment connectors such that the primary connectors form a first connection between the aircraft when the aircraft are flying in a connection pattern. Thereafter, retraction of the primary connectors reduces wingtip separation of the aircraft such that the alignment connectors form a second connection between the aircraft establishing coarse alignment therebetween. Thereafter, retraction of the primary and alignment connectors further reduces wingtip separation of the aircraft such that the male and female connector assemblies form a third connection between the aircraft establishing fine alignment therebetween.