The convection cooled (thetaJA) case is impractical to calculate
because you are unlikely to know the airflow where it counts.
Measuring it however can be pretty straightforward. You
first pull the Vbe vs temp at some reference current (or
reference setup, like power supply and resistor). Then you
light up the transistor as you'd run it, wait for temp to get
stable (few seconds for a low mass package, maybe a
minute or more with a big heat sink mass) and quickly
flip from forcing power, to force/measure Vbe. Refer Vbe
back to temnperature, and you know your power level
for the as-run condition, so there's your thermal impedance
and your junction temp rise. Junction to case you can then
get from the datasheet, if you care.