The emergence of less restricted fare structures in the airline industry reduced the capability of airlines to segment demand through restrictions such as Saturday night minimum stay, advance purchase, non-refundability, and cancellation fees. As a result, new forecasting techniques such as Hybrid Forecasting and optimization methods such as Fare Adjustment were developed to account for passenger willingness-to- pay. This thesis explores statistical methods for estimating sell-up, or the likelihood of a passenger to purchase a higher fare class than they originally intended, based solely on historical booking data available in revenue management databases. Due to the inherent sparseness of sell-up data over the booking period, sell-up estimation is often difficult to perform on a per-market basis. On the other hand, estimating sell-up over an entire airline network creates estimates that are too broad and over-generalized. We apply the K-Means clustering algorithm to cluster markets with similar sell-up estimates in an attempt to address this problem, creating a middle ground between system-wide and per-market sell-up estimation. This thesis also formally introduces a new regression-based forecasting method known as Rational Choice. Rational Choice Forecasting creates passenger type categories based on potential willingness-to-pay levels and the lowest open fare class. Using this information, sell-up is accounted for within the passenger type categories, making Rational Choice Forecasting less complex than Hybrid Forecasting. This thesis uses the Passenger Origin-Destination Simulator to analyze the impact of these forecasting and sell-up methods in a controlled, competitive airline environment. The simulation results indicate that determining an appropriate level of market sell-up aggregation through clustering both increases revenue and generates sell-up estimates with a sufficient number of observations. In addition, the findings show that Hybrid Forecasting creates aggressive forecasts that result in more low fare class closures, leaving room for not only sell-up, but for recapture and spill-in passengers in higher fare classes. On the contrary, Rational Choice Forecasting, while simpler than Hybrid Forecasting with sell-up estimation, consistently generates lower revenues than Hybrid Forecasting (but still better than standard pick-up forecasting). To gain a better understanding of why different markets are grouped into different clusters, this thesis uses regression analysis to determine the relationship between a market's characteristics and its estimated sell-up rate. These results indicate that several market factors, in addition to the actual historical bookings, may predict to some degree passenger willingness-to-pay within a market. Consequently, this research illustrates the importance of passenger willingness-to-pay estimation and its relationship to forecasting in airline revenue management.