Smart Shopping for Holidays

Overview

Smart Shopping for Holidays was a 2025 hackathon project where we prototyped an AI-powered trip planner that could turn a traveler’s loose intent into a concrete, bookable trip. In a few days, our team built a conversational “smart trip” experience that used Expedia's supply and loyalty context to suggest destinations and stays. Essentially an early, scrappy proof of concept for what later became the Smart Trip AI product direction.

Hackathon 2025

Stage

XD / Eng

Stakeholders

3 days / June 2025

Timeline

Problem

Travelers often miss opportunities to maximize their vacation days because combining national holidays with personal time off requires manual effort, searching online, checking calendars, and piecing together dates, making trip planning time-consuming, frustrating, and less inspiring.

Our mission is to help travelers unlock more vacation possibilities by smartly combining national holidays and personal time off, turning everyday breaks into extraordinary journeys

Outcome

The AI Smart Trips hackathon prototype proved that a conversational planner could turn vague trip ideas into concrete, bookable plans, earning strong internal feedback and helping shape early thinking for what later became our Smart Trip AI direction.

This work was carried through from discovery to delivery, shaped through multiple rounds of iteration, and is slated to ship in Q4 2026.

If you enjoyed the video and storytelling behind AI Smart Trips, feel free to reach out, I’m happy to share more.