A system and method to facilitate expansion, disambiguation, and optimization of search queries over a network wherein an original query received from a user is parsed to obtain at least one query term. One or more filtered queries are retrieved from a database, each of the filtered queries corresponding to one or more advertising offers related contextually to the at least one query term. Selection of advertising content associated with the advertising offers is optimized based on one or more predetermined parameters, the advertising content to be displayed for the user in conjunction with query results of the original query and the one or more filtered queries.