Trip Advisor has an interesting game called Traveler IQ Challenge.

I thought it was fun. 

On a related note, here are some of my favorite Travel sites.

Farecast:  This site has lots of nice features.  This link shows cheap fares from a city.  The graphic to the right shows other features to look for on that page.  For example:

• when to travel (which days have the lowest fares), and
• where to travel (which cities have the best deals).

Kayak: Search 140+ travel sites at once to find and compare the cheapest fares from all sites together – great grids and filters to find what you are looking for fast.

Airfare Watchdog:  Up-to-date list of low fares from major airlines (including Southwest).  You can subscribe to alerts too.