With Calgary Airport’s (YYC) growing passenger base bringing expansion of the passenger terminal and a fourth runway, the City of Calgary (City) had to decide whether to have the crossing through road, Airport Trail, to run as a continuous uninterrupted roadway; as the newly constructed runway will break Airport Trail into a discontinuous corridor. In February 2011, the decision was made by City Council to make Airport Trail continuous with a sub-lease agreement negotiated with YYC initiating the design and construction of the tunnel, along with a functional planning study of Airport Trail which this paper discusses. The planning of the corridor was atypical of standard freeway facilities. A major design challenge encountered in the study was a change in Airport Trail’s roadway classification from an arterial, which has more relaxed access and movement provisions, to the reclassified skeletal standard, which emphasizes on free-flow movement and on enhanced access management. Additional modelling effort was required at the onset of the study in order to allow Airport Trail to be designed to applicable volumes. Additionally, specific attention was required at constrained locations which involved geometric design decisions to provide safer and more efficient operations. Constraints include tunnel proximity, integrating high vehicle volumes and balancing the right-of-way requirements for vehicle and LRT inside the tunnel. As well, the design of Airport Trail was to be integrated with existing infrastructure including the construction of airport infrastructure. Challenges encountered during the study are outlined and their solutions described including lessons learnt from the project.