Results of Wizard of Oz experiments are presented using a Chilean Spanish version of the CU Communicator Travel Planning system in Chile. The experiments evaluated user responses during conversational interaction with the system to plan a domestic flight, and examined user impressions of a diphone text-to-speech synthesis system developed with speech samples from a Chilean speaker. Two synthesizers were employed, with and without pitch contour. The results showed a positive overall attitude toward the system, and that a proper pitch contour improves the subjective intelligibility of the synthesized speech.