Aviation operations place a high value on winds aloft data for safety reasons. Conventional methods such as radiosonde/rawindsonde soundings tend to be expensive and are also labor-intensive. In this paper we use image processing of sky image data from one or more ground based total sky imagers to derive winds at the boundary layer. Several different cloud motion methods are explored and evaluated, including the use of a single imager and co-located ceilometer. Specific emphasis was placed on a generalized method that can work under greatly differing sky conditions.