Last year I was playing with a plotting program for Mac OS X, which was pretty good, but not quite satisfactory. I've found a better one, Plot, which is free (as in beer), fairly easy to use, and very customisable. It has its own idiosyncrasies, but I like it a lot. Here's an example plot, showing how the top speed of British combat increased up to the end of the Second World War.
The data are drawn from John W. R. Taylor, Combat Aircraft of the World From 1909 to the Present (New York: Paragon, 1979). This excludes aircraft which never saw service as well as those not intended for combat (though not all actually saw combat). The year is that in which it entered service (usually with the RAF), or if this wasn't given, the year when the prototype first flew. (Some aircraft unfortunately had neither, and so were omitted.) The maximum speeds, in miles per hour, are not necessarily comparable, because they were often obtained at different heights; also, they may not have been sustainable under normal conditions. But they should be broadly indicative of real-world maximums. I've classified each aircraft as either fighters (red) or bombers (blue), based upon their actual use. However, that's fairly arbitrary for the period up to 1915, which is when aircraft adapted for specialised roles began to appear. I haven't included seaplanes but I have included carrier-borne aircraft. Generally, I have only included data for the most representative version (eg not for each of the innumerable marks of Spitfire). Because of these caveats and inconsistencies, the plot should not be taken too seriously -- it's just for illustrative purposes.