The box wing is an unconventional aircraft configuration that has the potential to provide major savings in fuel consumption relative to the conventional cantilever wing. In order to further develop and evaluate this potential, high-fidelity aerodynamic shape optimization is applied to the aerodynamic design of a box wing and a cantilever wing, based on the Embraer E190 regional jet, with the latter serving as a performance baseline. The optimization framework consists of B-spline parameterization, free-form and axial deformation geometry control, an integrated mesh-movement scheme based on the theory of linear elasticity, a Newton-Krylov-Schur flow solver for the Reynolds-averaged Navier-Stokes equations, a gradient-based optimizer, and the discrete-adjoint method for gradient evaluation. Results indicate that a box-wing with a heightto-span ratio of 0.26 burns 7.61% less fuel at cruise than a conventional baseline of the same span and lift. Aerodynamic trends and trade-offs are investigated, and a weight sensitivity study is performed.ii Acknowledgements First and foremost, I would like to thank my supervisor, Professor David Zingg. I cannot thank him enough for the opportunity to work on such a state-of-the-art problem, which has proven to be challenging, but incredibly rewarding. I also have him to thank for the invaluable knowledge and experience that I have gained during these past few years. His passion for computational aerodynamics and environmentally-friendly aircraft design is something to be envied, and will always serve as a pillar of inspiration. I would also like to thank the UTIAS community for creating a welcoming and fun work environment. To the computational aerodynamics group, thank you for all of the helpful feedback you have given me over the years, and for making my late nights in the lab palatable. In particular, I would like to thank Dr. Shahriar Khosravi for the many interesting discussions on aerodynamics and structures, and Dr. Thomas Reist for his invaluable technical guidance and discussions on aircraft design.