There are now a lot of good programs out for sight-reading, simple chord progression recognition, and for jazz, even some backing track creators. But is there a program that generates chord changes for drilling to improve your accuracy in reading lead sheets? It would be a plus if it is midi-enabled to evaluate your accuracy.
Interpreting jazz changes is far too subjective to allow for the possibility of software evaluating what you play on a MIDI keyboard, in my opinion. If you want to work on this, it would be better to just practice changes in actual tunes and use your ears to decide if you're getting it or not.
There are patterns that you can use to drill yourself, for example, the
If you need help learning how to voice different chords, I would recommend Mark Levine's The Jazz Piano Book, and transcribing voicings from the masters.
For practice of all of this, playing along with rhythm tracks is really it. You can either get Jamey Aebersold recordings (there are a few volumes specifically for piano), input changes (from a fake book or whatnot) into Band-in-a-Box, or my favorite, check out iReal b -- it's a backing track player that will display chord changes on your screen (iOS, OS X, or Android) while playing back piano, bass, and drums in whatever style, key, tempo, and instrument balance you choose (that is, you can mute the piano track). The best part about it is that there are some >1,000 sets of changes for existing tunes that can be downloaded for free immediately when you get the app, in addition to 50 different drill exercises like the
All I got is a link to Impro-Visor... It might fit your needs... You make little chord change "grammars" and such. http://www.cs.hmc.edu/~keller/jazz/improvisor