This paper presents an evaluation of runway operations at Chicago O’Hare International Airport to estimate the impact of proposed wake vortex separation including Recategorization Phase II and III dynamic separations. The evaluation uses a Monte Carlo simulation model that considers arrival and departure operations. The simulation accounts for static and dynamic wake vortex separations, aircraft fleet mix, runway occupancy times, aircraft approach speeds, aircraft wake circulation capacity, environmental conditions, and operational error buffers. Airport data considered for this analysis are based on Airport Surface Detection Equipment Model X records from Chicago O’Hare International Airport from January to November 2016. Dynamic wake separations are tailored to each unique set of conditions by using environmental and aircraft performance parameters as input and allowing aircraft to be exposed to the same wake vortex strength as in Recategorization Phase II (RECAT II). The analysis shows that further reductions beyond RECAT II for aircraft pairs separated by 2 nautical miles or less is not operationally feasible. These wake separations already result in little to no wake dependency. When this is the case, the challenges in wake separation are to meet runway occupancy times and to make sure aircraft separations allow for human operational variations without resulting in aircraft turnarounds or double-aircraft-occupancy runway violations.