There is one train daily from Yogyakarta to Blitar, leaving after midnight and arriving in the morning.
As per April 2010 the schedule is:
GAJAYANA, dep. 01:30, arr. 06:57, executive Rp 150,000
Schedule and prices may be different on holidays. You can check for yourself on: http://kereta-api.co.id/ . The site is in Indonesian, but you need only to fill in on the right: Tanggal = , Asal = Yogyakarta, Tujuan = Madiun, then click [Tampilkan].
the closest entry points to reach blitar by air are from surabaya and malang. then from these points continued with train or bus or car service called "travel" which have door-to-door service.
long time ago, before the tragedy of hot muds of lapindo brantas co., that flooding onto more than 20 villages at porong on the way to malang and sidoarjo, the surabaya enroute to blitar was nice. even take longer time than malang as an approaching point.
now, the best enroute from surabaya as follows: surabaya-krian-mojokerto-mojoagung-jombang-kediri-blitar