Smart Trip AI™ Trip Planner
Overview
Smart Trip AI™ is a conversational trip planner that transforms fuzzy travel ideas into bookable hotels and activities, right on partner loyalty sites, an AI companion that makes every trip smarter, faster, and easier to plan.
Shipped / Beta / Nov'25
Stage
XD / XR / CD / PM / Eng / Data Sci
Stakeholders
July 2025 - present
Timeline
Traveler context
Travelers were already experimenting with generic AI tools, typing prompts into chatbots, then manually hunting through tabs to find matching hotels and activities on our partners’ sites. The intent and curiosity were there, but the planning work (and often the eventual booking) leaked out into tools we didn’t control.
Partner context
At the same time, our partners wanted to prove the value of their loyalty programs, not just with points balances, but with smarter, more personal help. SmartTrip AI was our answer: a conversational planner that could sit quietly on their homepages until it was needed, then step in as a co-pilot for hotels and activities.
Problem
Travelers face an overwhelming and time-consuming trip planning process filled with scattered information, conflicting recommendations, and difficulty creating a truly personalized itinerary.
Traveler
Trip planning is exciting but time-consuming
Partner
Need tools that drive bookings and keep users engaged.
Business
Grow scalable AI experiences across brands
Opportunity
Traveler
Help travelers move from “I kind of want to go somewhere warm” to a short list of bookable hotels and things to do that genuinely fit their constraints.
Partner
Measure Smart Trip AI’s impact by tracking engagement (impressions, opens, messages exchanged, time in experience, bounce rate, and repeat visitors) alongside conversion outcomes,
Business
Drive higher engagement on partner sites by giving travelers a reason to start planning there, not elsewhere.
Early design explorations
Further Ideation + Iterations
For this phase, I zoomed in on the entry point itself, treating the Smart Trip AI tab as a tiny product that had to earn a click. I explored variations in copy, hierarchy, and CTA framing to see how far I could push clarity “what does this do?”, confidence “is this safe to try?”, and effort “how much do I have to type?”, from a simple “Ask anything” prompt to more guided microcopy that gently explained what Smart Trip AI could and couldn’t help with.
Finalized version
In the Smart Trip AI journey, travelers can start from the WLT search widget through a Smart Trip AI tab. From there, they land in a full-sheet conversational view with clear AI disclaimers and a short welcome, then share their intent in natural language anything from dates and destinations to budgets, constraints, or simply “surprise me.” In response, Smart Trip AI returns structured hotel and, for some partners, activity recommendations as scannable cards (typically five per line of business), each with “view details” and “view more” actions, pricing, and earn messaging today, plus burn scenarios and points-only views in the upcoming roadmap.
Outcomes & impact
Smart Trip AI is still evolving, but the MVP and post MVP phases already established a shippable, partner-ready AI planner, with embedded AI disclaimers, hotel and activity recommendations enriched with earn messaging, and white-label entry points tailored for partners like Delta, AirNZ, AARP and more backed by a clear metrics framework for engagement, conversion, satisfaction, and repeat use. We also aligned the roadmap with broader platform work, so Smart Trip AI actively shaped the underlying capabilities rather than working around them. Within the design org, it became a reference pattern for how we build agentic AI experiences in B2B2C contexts, balancing traveler trust, partner brand, and platform constraints.
