I've hooked up my ipod to the Dewalt construction radios before. It seems like the digital read out for radio goes crazy on them. They do spend the cold nights in the barn and what not. What is another option?
They make these things called wireless speakers, I won a Milwaukee job site speaker at the company picnic, can hook the I pad to it or wireless from the phone works great. Klein Tools has one that is about the size of a tape measure but the sound that comes out of it is pretty good.