You may be right about the relationships, and without that Hipmunk is vulnerable, but I think you're dead wrong about the UI.
The fact that old people don't "get" it just means they are used to the old UIs regardless of how crappy they are (a lot of them still call a travel agent due to sheer annoyance at the complexity of booking flights online). Most people do want the information that Hipmunk puts at your fingertips, and over time it will spread by word of mouth, and the younger generation who easily groks this type of UI will replace the aging population who hasn't grown up with deep data visualizations in their every day life.
Not every flight search is terrible on Orbitz/Expedia/Kayak, but I've done a few where all I could see was shit flights for pages and pages of results, and one search on Hipmunk yielded an obviously superior and amazing itinerary for $10 more.
Hipmunk may be weak on the pure business side, but they are one in a million on the UI side, and I predict that strength will take them places.
The fact that old people don't "get" it just means they are used to the old UIs regardless of how crappy they are (a lot of them still call a travel agent due to sheer annoyance at the complexity of booking flights online). Most people do want the information that Hipmunk puts at your fingertips, and over time it will spread by word of mouth, and the younger generation who easily groks this type of UI will replace the aging population who hasn't grown up with deep data visualizations in their every day life.
Not every flight search is terrible on Orbitz/Expedia/Kayak, but I've done a few where all I could see was shit flights for pages and pages of results, and one search on Hipmunk yielded an obviously superior and amazing itinerary for $10 more.
Hipmunk may be weak on the pure business side, but they are one in a million on the UI side, and I predict that strength will take them places.