Methods and systems for analyzing, ranking, and presenting multi-modality transportation proposals are presented. In one embodiment, a method is provided that includes receiving a request for transportation and generating proposals that include routes for transportation an origin location and a destination location of the request. The proposals each include segment(s) corresponding to a portion of a route and at least one modality identifying a type of transportation for the segment(s). Proposal scores may then be calculated for each of the proposals. Proposal scores for a proposal may be calculated based on a disutility measure of the proposal that measures a predicted inconvenience for a user following the route identified by the proposal. The proposals may be ranked based on the proposal scores and the ranking may be transmitted to a mobile device for display on the mobile device.