Embodiments of the present invention provide optimization of telephone services through telephone calling plan/card analysis. The least expensive rate is found for telephone calls at any given time and/or date, either through static pre-entry of data, or through dynamic querying of rates via a web-based look-up table, and places calls according to an optimized calling plan. Specifically, in a typical embodiment, an outgoing/target telephone number for an intended telephone call is captured, and a corresponding destination geographic region is identified. Based on the geographic region, a calling plan resulting in a lowest price for the telephone call is identified. This is typically accomplished by consulting at least one table (e.g., call information table) that associates (among other things) calling plans and/or calling cards with geographic regions. Once a calling plan and/or calling card is identified/selected, a corresponding set of dialing instructions will be obtained from the table and used to make/place the telephone call.