Imagine you want to take a trip this weekend and you don't mind too much where you're going as long as the price isn't crazy. Lets call people that fit this persona "the weekend traveller".
Currently Airlines and Online Travel Agents (OTAs) make this a pretty time-consuming task by requiring us to make multiple searches for different locations and manually note the information that we find.
As an example, take jetBlue (an airline that I think has one of the best online booking experiences):



For a traveller who wants to get to a specific location on a specific time I think jetblue has a great flow without any serious usability issues.
The problem for a weekend traveler with no set destination in mind, is the experience is simply exhausting. Hundreds of interactions must be completed before all options are reviewed and more likely that not people will give up before they find an interesting deal.
One possibility to avoid this experience is to create a highly specialized search experience for the the weekend leisure traveller.
For this person we can make three assumptions:
To explore this idea I created an HTML prototype for a search experience tailored for the weekend traveler persona .
Using the smart defaults results can be shown immediately. By default results are sorted by lowest price first and showing all destination cities.
In the demo prototype, Fort Lauderdale has a great flight deal ($34 for return flights from Boston) but the weather is forecast for thunderstorms.

To escape the heat wave of the Boston summer sorting is changed to view locations with the coolest temperature, but filtered to show only the destinations with pleasant weather (sunny or partially sunny on both days).
In the demo prototype, San Francisco has the coolest fine weather, but at over 6 hours away Detroit at only $87 is an option that might not have been considered as a great weekend destination but with the weather and price combined warrants further investigation.

A list of destinations that can easily be scanned helps encourage exploration of places that a traveller might not have previously considered. Adding information about expected weather helps the traveler make an informed decision removing anxiety and friction for moving onto the next stage of booking.
Additional information and ancillary sales (e.g. hotel accommodation, rental cars and attractions) could also be presented as information and items be bundled into the purchase.
The prototype uses static data for weather and flight prices and is not accurate. However sorting and filtering does work. Please try the prototype and let me know any feedback or ideas you have!
Try Prototype