For me, part of the fun of traveling is planning it beforehand and looking back on it afterward. There are several online tools that allow you to visualize this data, some better than others. GCmap Flight Diary Flight Memory
One of the best tools to use when planning a flight is GCmap which stands for great circle map. It’s useful because calculating distances on a sphere is kinda hard and this makes it easy and for showing the actual flight path since the shortest distance between two points isn’t a straight line. You can type in an individual airport code, or a string of codes to visualize flight paths and check distances. This is especially useful for award flights dependent on distance like Avios and ANA awards. The best part is that the maps can be controlled entirely from the URL meaning you can integrate flight maps into your own program my simply formatting a string with the correct variables. To generate this map I typed in: lax-ord-jfk-mia, tul, iah
The long time frontrunner for keeping track of flights was Flight Memory which was founded in 2005. It seems to be what most long time flight enthusiast use and it does a decent job of calculating flight stats, but leaves a little to be desired for user interface.
However, I’ve saved my favorite for last: flight diary. It’s difficult to find online unless you google the exact name, but it’s worth it when you find it (and hopefully bookmark it). It does a much nicer job of displaying data and maps than Flight Memory and has a much nicer user interface. My only complaint is that it breaks up the different models of airplanes (737, 738, 73X, etc.) instead of calling them all a 737 which they essentially are for my tracking purposes.
Update 6/3:
After entering all my upcoming plans on Flight Diary, I realized that there was an error with the way it calculates airports. Say I fly TUL-DEN-SFO. It should count each airport once. Instead, it counts Denver twice which explains why it shows I’ve been to Denver so often.
I decided to import all of my data into Flightmemory and see if it calculated airports the same way. Before now, I’d seen plenty of Flightmemory stats but never used it myself since I prefer the nicer looking Flight Diary. Flight Diary makes it easy to import and export your data so I assumed the Flightmemory would also have an import/export function. Turns out you can import data, but it’ll cost you at least $30. It looks like they are probably doing this by hand instead of automating it. I can’t really advocate using a service that won’t let you import or export your data.