Winglets and wingtip structures have been prominent in commercial aircraft design in the past few decades. These designs are known to reduce the induced drag on an aircraft wing, thus increasing its overall fuel efficiency. Several different winglet designs exist, and little reason is offered as to why different winglet designs are used in practice on different aircraft, especially those of variable range. This research tests existing winglets (no winglet, raked winglet, flat plate winglet, blended winglet, and wingtip fence) on a span-constrained wing planform design both computationally and in the wind tunnel. While computational tests using a vortex lattice code indicate that the wingtip fence minimizes induced drag and maximizes lift to drag ratio in most cases, wind tunnel tests show that at different lift coefficients and angles of attack, the raked winglet and blended winglet optimize the aerodynamic efficiency at incompressible flow velocities. Applying the wing aerodynamic data to existing variable range commercial aircraft, mission performance analysis is run on a Bombardier CRJ200, Airbus A320, and Airbus A340-300. By comparing flight lift coefficients in cruise for these aircraft to the lift coefficients at which winglets minimize drag in compressible flows, optimal winglet designs are chosen. It is found that the short range CRJ200 is best equipped with a flat plate or blended winglet, the medium range A320 can reduce drag with either a wingtip fence, raked winglet, or blended winglet, and the long range A340 performs best with a flat plate, blended, or raked winglet. Overall, despite the discrepancy in winglet selection depending on which experimental results are used, it is clear that addition of a winglet to a span-constrained wing is beneficial in that it reduces induced drag and therefore increases overall fuel efficiency.